安藤 香織

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アバター
研究者氏名
安藤 香織
 
アンドウ カオリ
所属
岐阜大学
部署
工学部 化学・生命工学科 生命化学コース
職名
教授

プロフィール

HWE 反応を用いるシス選択的オレフィン合成/HWE反応は一般に高いトランス選択性でオレフィンを与える。本研究ではHWE試薬の置換基を換える事により高い選択性でシスオレフィンを与える方法の開発を行なっている。/分子軌道計算を用いる有機反応の立体制御因子の解明/有機反応が起こる際、どのような因子によって立体選択性が制御されているのかを、分子軌道計算により反応の遷移状態を調べることにより解明する研究。/新しいJulia-Kocienski試薬の開発/Peterson反応を用いるシス-α,β-不飽和スルホンの合成/C-H活性化機構の解明

研究分野

 
 

経歴

 
2007年4月
 - 
2017年6月
岐阜大学 工学部 教授
 
2004年4月
 - 
2007年3月
琉球大学 教育学部 教授
 
1993年4月
 - 
2004年3月
琉球大学 教育学部 助教授
 
1988年4月
 - 
1993年3月
帝京大学 薬学部 助手
 
1986年4月
 - 
1987年1月
マサチューセッツ工科大学化学科
 

学歴

 
1981年4月
 - 
1983年3月
東京大学理学系大学院修士課程化学専攻  
 

受賞

 
1996年2月
東レ研究企画賞
 

論文

 
Highly Selective Recognition of Cytosine over Urasil and Adenine by a Guanine Analog, 2-N-Acetyl-3-deazaguanine, in 2’-O-Methyl-RNA/RNA Duplexes
Seio Kohji(Crest, JST),Sasami Takeshi(Crest, JST),Ohkubo Akihiro(Crest, JST),Ando Kaori(College of Education, University of the Ryukyus),Sekine Mitsuo(Dept. of Life Science, Tokyo Institute of Technology)
J. Am. Chem. Soc.   129巻(5号) 1026-1027   2007年1月
Synthesis of hetero- and carbocycles by nucleophilic substitution at sp2 carbon
Miyauchi Hironori(Dept. of Chemistry, The University of Tokyo),Chiba Shunsuke(Dept. of Chemistry, The University of Tokyo),Fukamizu Koji(Dept. of Chemistry, The University of Tokyo),Ando Kaori(Dept. of Applied Chemistry, Gifu University),Narasaka Koichi(Dept. of Chemistry, The University of Tokyo)
Tetrahedron   63(26) 5940-5953   2007年6月
Chemical synthesis of RNA via 2'-O-cyanoethylated intermediates
Saneyoshi Hisao(Crest, JST),Ando Kaori(Dept. of Applied Chemistry, Gifu University),Seio Kohji(Crest, JST),Sekine Mitsuo(Dept. ofLife Science, Tokyo Institute of Technology)
Tetrahedron   63(45) 11195-11203   2007年11月
Pentacoordinate Organoantimony Compounds that isomerizes by Trunstile Rotation
安藤 香織(岐阜大学工学部)
J. Am. Chem. Soc.   3418-3419   2009年3月
Z-selective intramolecular Horner-Wadsworth-Emmons reaction for the synthesis of macrocyclic lactones.
Ando Kaori(Gifu University),Narumiya Kenji(Gifu University),Takada Hiroaki(Gifu University),Teruya Taiji(Ryukyu University)
Organic Letters   131 1460-1463   2010年3月

Misc

 
┣DBKaori Ando(/)-┫DB ; Preparations of Ζ-α,β-Unsaturated Amides by Using Horner-Wadsworth-Emmons Reagents, (Diphenylphosphono) acetamides
Synlett   1272-1274   2001年
┣DB安藤香織(/)-┫DB;Ζ-選択的Horner-Wadsworth-Emmons反応
有機合成化学協会誌   58 869-876   2000年
A Highly cis-Selective Synthesis of 2-Ethylmylaziridines by Intramolecular Amination of Chiral Bromoallenes: Improvement of Stereocelectivity Based on the Computatunal Investigation
J. Am. Chem. Soc.   web release date; Nov.28, 2002    2002年
Hiroaki Ohno, Kaori Ando, Hisao Hamaguchi, Yusuke Takeoka, Tetsuaki Tanaka
Journal of the American Chemical Society   124 15255-15266
The base-mediated intramolecular amination of bromoallenes having an axial chirality is described. The treatment of (4S,aR)-4-alkyl-4-[N-(arylsulfonyl)amino]-1-bromobuta-1,2-dienes with NaH in DMF affords 2,3-cis-2-ethynylaziridines in good to exc...
ANDO K
J. Org. Chem.   64(18) 6815-6821
The mechanism of the Horner-Wadsworth-Emmons (HWE) reaction has been investigated using ab initio calculations (RHF/6-31+G*). This study revealed that the HWE reaction of the lithium enolate derived from trimethyl phosphonoacetate with acetaldehyd...
Kaori Ando
Journal of the American Chemical Society   127 3964-3972
The alkylation of 4-methoxymethyl-γ-butyrolactone enolate with methyl chloride was studied at the B3LYP/6-31+G* level. Conformer search of the free enolate gave 15 unique conformers within 5.39 kcal/mol. The transition structures for both anti- an...
Kenzi Hori, Akio Kamimura, Kaori Ando, Miyuki Mizumura, Yasuji Ihara
Tetrahedron   53 4317-4330
The alkaline hydrolysis of amides, N-methyl acetamide 1, acetanilide 2, and N-acetyl imidazole 3, was investigated by use of ab initio molecular orbital calcuIations. A detailed analysis was performed for two possible mechanisms, Path 1 and 2. Pat...
William R. Roush, Alan D. Palkowitz, Kaori Ando
Journal of the American Chemical Society   112 6348-6359
Double asymmetric reactions of the tartrate ester modified crotylboronates 1 and 2 and α-methyl chiral aldehydes are described. The reactions of the appropriate enantiomers of 1 and 2 with β-alkoxy-α-methylpropionaldehydes 11 provide adducts 12, 1...
Kaori Ando, Naoki Akadegawa, Hiroaki Takayama
J. Chem. Soc. , Perkin Trans. 1   2263-2268   1993年12月
Alkylation of 4H,6H-thieno[3,4-c]furan 5,5-dioxide (furan-annulated sulfolene) 1 readily gave its 4-alkyl, 4,6-dialkyl, or 4,4-dialkyl derivatives, selectively. Attempts were made to use the appropriate derivatives as 3,4-dimethylenefuran synthons...
Kaori Ando, Naoki Akadegawa, Hiroaki Takayama
Journal of the Chemical Society, Chemical Communications   1765-1767
4H,6H-thieno[3,4-c]furan 5,5-dioxide 1 was readily converted to the 4-alkylated compounds 2 and the appropriate compounds 2 were submitted to intramolecular Diels-Alder reactions to afford fused furans 8a and b in good yields.
安藤 香織, 小池 文明, 近藤 文博, 高山 浩明
Chem. Pharm. Bull.   43(2) 189-192   1995年
K. Ando, F. Koike, H. Takayama
Chemical and Pharmaceutical Bulletin   43 189-192   1995年1月
An improved synthesis of a highly potent vitamin D3 analog, 24,24-difluoro-1α,25-dihydroxyvitamin D3 (1b) has been accomplished via vitamin D2-SO2 adducts. The introduction of fluorine atoms was performed by treating the α-keto ester (11) with die...
K. Ando, F. Kondo, F. Koike, H. Takayama
Chemical and Pharmaceutical Bulletin   40 1662-1664
An improved synthesis of a highly potent vitamin D3 analog, 24,24-difluoro-1α,25-dihydroxyvitamin D3 has been accomplished. The total yield was 9.3% from inexpensive vitamin D2 in 11 steps.
Kiyoshi Tomioka, Kaori Ando, Yutaka Takemasa, Kenji Koga
Journal of the American Chemical Society   106 2718-2719
William R. Roush, Kaori Ando, Daniel B. Powers, Alan D. Palkowitz, Ronald L. Halterman
Journal of the American Chemical Society   112 6339-6348
Diisopropyl tartrate modified (E)- and (Z)-crotylboronates 2 and 3 are easily prepared with very high isomeric purity (≥98% E for 2; ≥99% Z for 3) via the metalation of (E)- and (Z)-2-butene with n-BuLi and KOtBu in THF followed by treatment of th...
Kaori Ando, Shigeo Nagaya, Yuko Tarumi
Tetrahedron Letters   50 5689-5691
New Horner-Wadsworth-Emmons reagents, (o-t-BuPhO)2P(O)CH2CONMe(OMe) and (o-t-BuPhO)2P(O)CH2CON(CH2CH2) 2O were prepared via the Arbuzov reaction in good yields. The HWE reaction of these reagents with a variety of aldehydes gave cis-α,β-unsaturate...
Natsuhisa Oka, Renpei Higashida, Yuji Takayama, Kaori Ando, Takeshi Wada
Nucleic acids symposium series (2004)   111-112   2011年5月
Nucleoside H-boranophosphonates were synthesized via the condensation reactions of appropriately protected nucleosides with monopyridinium H-boranophosphonate and subsequent deprotection under basic conditions. 3',5'-O-Protected dinucleoside H-bor...
Hisao Saneyoshi, Hisao Saneyoshi, Kaori Ando, Kohji Seio, Kohji Seio, Mitsuo Sekine, Mitsuo Sekine
Tetrahedron   63 11195-11203
It was found that 2′-O-cyanoethyl group could be removed from 2′-O-cyanoethylated ribonucleoside derivatives by treatment with Bu4NF. This finding was successfully applied to the synthesis of oligoribonucleotides via their 2′-O-cyanoethylated deri...
Kiyoshi Tomioka, Wonjun Seo, Kaori Ando, Kenji Koga
Tetrahedron Letters   28 6637-6640
By the promotion of chlorotrimethylsilane, asymmetric Michael reaction of the chiral enamines (2) of α-alkyl β-keto esters (1) with methyl vinyl ketone and ethyl acrylate proceeded to afford, after hydrolysis, either enantiomer of the correspondin...
Shunsuke Chiba, Kaori Ando, Koichi Narasaka
Synlett   2549-2564
In this account, recent advances on nucleophilic substitution reactions at sp(2) hybridized carbons of lithium alkylidene carbenoids and simple vinyl halides are described. 1 Introduction 2 Nucleophilic Substitution Reactions of Lithium Alkylidene...
Kaori Ando, Keiji Morokuma, Keiji Morokuma
Theoretical Chemistry Accounts   130 323-331
DFT computational study on the alkylation of the lithium enolate derived from acetaldehyde with MeCl was performed. The reaction of the free enolate CH2=CHO- with MeCl has an early transition state with low barrier, and the reaction of its lithium...
Tsuyoshi Satoh, Yumi Ogino, Kaori Ando
Tetrahedron   61 10262-10276
1-Chlorovinyl p-tolyl sulfoxides were synthesized from ketones and chloromethyl p-tolyl sulfoxide in high yields. Treatment of the sulfoxides with isopropylmagnesium chloride at -78°C in toluene gave magnesium alkylidene carbenoids (α-chloro alken...
Takayuki Goto, Takayuki Goto, Koji Takeda, Masahiro Anada, Kaori Ando, Shunichi Hashimoto
Tetrahedron Letters   52 4200-4203
The first successful example of a catalytic asymmetric cyclopropanation with α-diazopropionates is described. The cyclopropanation reaction of 1-aryl-substituted and related conjugated alkenes with tert-butyl α-diazopropionate has been achieved by...
William R. Roush, William R. Roush, Kaori Ando, Kaori Ando, Daniel B. Powers, Daniel B. Powers, Ronald L. Halterman, Ronald L. Halterman, Alan D. Palkowitz, Alan D. Palkowitz
Tetrahedron Letters   29 5579-5582
The reactions of diisopropyl tartrate modified( E)- and (Z)-crotylboronates with representative achiral aldehydes are described. Enantioselectivity ranges from 55-91% e.e. depending on the aldehyde employed. © 1988.
ANDO K, HOUK K N, BUSCH J, MENASSE´ A, SE´QUIN U
4. Org. Chem.   63(6) 1761-1766
The stereochemistries of nucleophilic additions of several hydride, methyl, and acetylenic Grignard and lithium reagents to hindered cyclohexanones were investigated experimentally. Acetylenic ' reagents attack hindered cyclohexanones from the axi...
Kaori Ando, Tomoe Egami
Heteroatom Chemistry   22 358-362
The three-component reaction of aldehydes, amines and triethyl or diphenyl phosphite was efficiently catalyzed by magnesium dodecyl sulfate at room temperature in water to give various α-amino phosphonates in high yields. The catalyst is easily av...
Kiyoshi Tomioka, Kaori Ando, Yutaka Takemasa, Kenji Koga
Tetrahedron Letters   25 5677-5680
Complementary asymmetric alkylation reaction of the lithioenamine derived from 2-methoxycarbonylcyclohexanone and (S)-valine tert-butyl ester was examined by employing the various electron pair donating additives in a toluene solvent, in order to ...
Kaori Ando, Hiroaki Takayama
Heterocycles   37 1417-1439
This review deals with our recent works 1 on the preparation of heteroaromatic-fused 3-sulfolenes (5) and their chemistry, especially Diels-Alder reactions with several dienophiles under thermal or high pressure conditions. Related chemistry of th...
Takayuki Goto, Koji Takeda, Naoyuki Shimada, Hisanori Nambu, Masahiro Anada, Motoo Shiro, Kaori Ando, Shunichi Hashimoto
Angewandte Chemie - International Edition   50 6803-6808
Two rhodium(II) ions work together: [Rh2(S-tbpttl)4] is an exceptionally effective catalyst for enantioselective cyclopropenation reactions of 1-alkynes with α-alkyl-α-diazoacetates (see scheme). Cyclopropenation is preferred over alkene formation...
Kaori Ando, Kyohei Yamada
Green Chemistry   13 1143-1146   2011年5月
The solvent-free Horner-Wadsworth-Emmons reaction of triethyl phosphonoacetate with a variety of aldehydes was catalyzed by DBU in the presence of K2CO3 to give E-α,β-unsaturated esters highly selectively (99:1 for most of the reactions). The reac...
Kohji Seio, Kohji Seio, Takeshi Sasami, Takeshi Sasami, Akihiro Ohkubo, Akihiro Ohkubo, Kaori Ando, Mitsuo Sekine, Mitsuo Sekine
Journal of the American Chemical Society   129 1026-1027
In this paper, we report a new modified base, 2-N-acetyl-3-deazaguanine (a2c3G), and the synthesis of the 2′-O-methyl-RNA incorporating a2c3G. It should be noted that a2c3G is the first example of guanine analogues that recognize cytosine more sel...
ANDO K
J. Org. Chem.   62(7) 1934-1939
New Horner-Emmons reagents, ethyl (diarylphosphono)acetates 1, were prepared from triethyl phosphonoacetate, PCl5 the corresponding phenols. The reaction of 1 with several kinds of aldehydes in the presence of Triton B or NaH in THF solvent reveal...
Kaori Ando, Miho Okumura, Shigeo Nagaya
Tetrahedron Letters   54 2026-2028
A new HWE reagent, (o-tBuC6H4O)2P(O)CH2CN (2e), reacts with various types of aldehydes to give Z-a,bunsaturated nitriles with 86% to >99% Z-selectivity. Especially, the reaction of 2e with bulkier aldehydes, both aromatic and aliphatic, gave the Z...
Intramolecular Substitution Reaction of Alkylidene-Lithium Carbenoids: Regioselective Synthesis of Indenenes
Helv. Chim. Acta.   85, 3130-3135    2002年
Hideyuki Yanagisawa, Kasei Miura, Mitsuru Kitamura, Koichi Narasaka, Kaori Ando
Helvetica Chimica Acta   85(10) 3130-3135
Intramolecular substitution reaction of geminal dibromo alkenes proceeds to afford indenes, dihydronaphthalenes, dihydrofurans, and dihydropyran via in sint generated lithium alkylidene carbenoids, which have a carbon or oxygen nucleophilic moiety...
Hideyuki Yanagisawa, Kasei Miura, Mitsuru Kitamura, Koichi Narasaka, Kaori Ando
Bull. Chem. Soc. Jp.   76(10) 2009-2026   2003年10月
When 4,4-dibromo-3-alkenols are treated with butyllithium, an intramolecular substitution reaction with alkoxide moiety occurs at the lithium alkylidene carbenoid center to give dihydrofurans. The reaction mechanism of this intramolecular substitu...
Kaori Ando
Journal of Organic Chemistry   75 8516-8521
The reaction mechanism of the AuCl-catalyzed reaction of the α-thioallenes to give 2,5-dihydrothiophenes has been computationally studied using DFT (B3LYP/6-31G*, SDD for Au). Calculations indicate the complexation of α-thioallene with AuCl occurs...
ANDO K, KANKAKE M, SUZUKI T, TAKAYAMA H
Tetrahedron   51(1) 129-138
New building blocks, 3,5-dihydro-1H-thieno[3,4-c]pyrrole 2,2-dioxides 3, have been prepared by the oxidation of their corresponding pyrroline derivatives 4 with DDQ or Chemical MnO2. The Diels-Alder reaction of 3 with dimethyl acetylenedicarboxyla...
Kaori Ando, Mutuo Kankake, Takayoshi Suzuki, Hiroaki Takayama
Journal of the Chemical Society, Chemical Communications   1100-1102
New building blocks, 3,5-dihydro-1H-thieno[3,4-c]pyrrole 2,2-dioxides 1, have been prepared and react with dimethyl acetylenedicarboxylate to give new types of compound: 7-aza-2,3-dimethylenenorbornene A, the 1:2 adduct B, 1a,3a,6,9-tetrahydrobenz...
Kaori Ando, Yusaku Suzuki
Tetrahedron Letters   51 2323-2325
New polymer-supported phosphonate reagents have been prepared and evaluated for the synthesis of Z-α,β-unsaturated esters. High Z-selectivity was obtained using the reagent having two o-t-BuC6H4 groups. © 2010 Elsevier Ltd. All rights reserved.
Kaori Ando, Chiharu Hatano, Naoki Akadegawa, Atsushi Shigihara, Hiroaki Takayama
Journal of the Chemical Society, Chemical Communications   870-873
4-Acyl-4H,6H-thieno[3,4-c]furan 5,5-dioxides have been prepared and submitted to Diels-Alder reactions to afford dienes with greater steric congestion after desulfonylation.
Mao Yi Lei, Koji Fukamizu, Yong Jun Xiao, Wei Min Liu, Scott Twiddy, Shunsuke Chiba, Kaori Ando, Koichi Narasaka
Tetrahedron Letters   49 4125-4129
Various 2-alkylidenethietanes were synthesized by intramolecular nucleophilic substitution reactions at an sp2 carbon of vinyl halides with thiolate moieties. The reaction pathway of the substitution reactions was confirmed as a very rare SNVπ mec...
Mao Yi Lei, Yong Jun Xiao, Wei Min Liu, Koji Fukamizu, Shunsuke Chiba, Kaori Ando, Koichi Narasaka
Tetrahedron   65 6888-6902
This article presents a full account of intramolecular vinylic substitution reactions of bromoalkenes having an acetylthio moiety, which give sulfur-containing heterocycles such as dihydrothiophene, tetrahydrothiopyran, and 2-alkylidenethietane de...
Masaaki Yoshifuji, Kaori Ando, Kozo Toyota, Ichiro Shima, Naoki Inamoto
Journal of the Chemical Society, Chemical Communications   419-420
The dechlorination reaction of the phosphonic dichloride ArP(O)Cl 2 (Ar = 2,4,6-But 3C6H2) with magnesium gave the sterically protected diphosphene oxide ArP(O) = PAr as a stable compound.
Shiro Matsukawa, Shiro Matsukawa, Shiro Matsukawa, Hideaki Yamamichi, Hideaki Yamamichi, Hideaki Yamamichi, Yohsuke Yamamoto, Yohsuke Yamamoto, Yohsuke Yamamoto, Kaori Ando, Kaori Ando, Kaori Ando
Journal of the American Chemical Society   131 3418-3419
Two stereoisomers of pentacoordinate antimony compounds (stiboranes) with a new rigid tridentate ligand were synthesized, and the isomerization was found to proceed by the turnstile rotation (TR) mechanism with the tridentate ligand as a trio and ...
Kaori Ando, Takahisa Kobayashi, Nariaki Uchida
Organic Letters   17 2554-2557
© 2015 American Chemical Society. (Chemical Presented). A new Julia-type methylenation reagent, 1-methyl-2-(methylsulfonyl)benzimidazole (1e), reacts with a variety of aldehydes and ketones in the presence of either NaHMDS (-55 °C to rt) or t-BuOK...
ANDO K
Tetrahedron Letters   36(23) 4105-4108
A new Horner-Emmons reagent, ethyl diphenylphosphonoacetate 1 was prepared from triethyl phosphonoacetate, PCl5, and phenol in 60% overall yield. Horner-Emmons reactions of 1 with aldehydes in the presence of Triton® B or NaH in THF gave the Z-uns...
K. Nagase, K. Ando-Nagase, Z. N. Kain, I. Maranets
Anesthesia and Analgesia   91 250
K. Ando
Synlett   1272-1274
New Horner-Wadsworth-Emmons reagents (diphenylphosphono)acetamides 2 react with a variety of aldehydes to give the corresponding Z-α,β-unsaturated amides stereoselectively (up to Z:E = 98: 2).
Yuichiro Nomura, Yumiko Onda, Satoshi Ohno, Hiroki Taniguchi, Kaori Ando, Natsuhisa Oka, Kazuya Nishikawa, Takashi Yokogawa
Protein Expression and Purification   88 13-19
Many archaeal tRNAs have archaeosine (G+) at position 15 in the D-loop and this is thought to strengthen the tertiary interaction with C48 in the V-loop. In the first step of G+ biosynthesis, archaeosine tRNA-guanine transglycosylase (ArcTGT)1 cat...
BEHNAM S M, BEHNAM S E, ANDO K, GREEN N S, HOUK K N
J.Org.Chem.   65(26) 8970-8978
The stereoselectivities of base-catalyzed enolizations of ketones have been studied by quantum mechanical methods. Transition structures of exo and endo deprotonation of camphor, norcamphor, and dehydronorcamphor have been located with two model b...
Frances H. Bayliffe, Alan Steven, Kaori Ando, Michael Shipman
Synlett   26 1371-1374
The effect of the halogen on the rate of sodium amide induced cyclization of 2-haloprop-2-enylamines to methyleneaziridines is studied. Using DFT calculations and competition experiments, it is shown to proceed faster using iodide-based substrates...
Kaori Ando, Kyohei Yamada
Tetrahedron Letters   51 3297-3299
The solvent-free Horner-Wadsworth-Emmons reaction with a variety of aldehydes using 1.5 equiv of DBU gave E-α,β-unsaturated esters and ketones in high yields. The E-selectivity was high and the used DBU was recovered. © 2010 Elsevier Ltd. All righ...
Kaori Ando, Kousuke Yasuda, Kiyoshi Tomioka, Kenji Koga
Journal of the Chemical Society, Perkin Transactions 1   277-282
Asymmetric Michael reaction of the chiral enamines prepared from α-alkyl β-keto esters and (S)-valine tert-butyl ester is described. The diastereoselectivity of this reaction is highly sensitive to the solvent system. The lithiated chiral enamines...
ANDO K, TAKEMASA Y, TOMIOKA K, KOGA K
Tetrahedron   49(8) 1579-1588   1993年1月
Asymmetric alkylation reaction of chiral enamines prepared from α-alkyl β-keto esters and (S)-valine tert-butyl ester leading to either enantiomer is described. Lithiated chiral enamines can be alkylated with alkyl halides in a toluene solvent in ...
Stereoselective reactions. XXIII. Asymmetric Michael reaction of α-alkyl β-keto esters via chiral enamines. Dependence of the diastereoface selection on the combination of solvents and additives
J. Chem. Soc. , Perkin Trans. 1   277-282   1994年
ANDO K, SEO W, TOMIOKA K, KOGA K
Tetrahedron   50(46) 13081-13088   1994年1月
Chlorotrimethylsilane promoted asymmetric Michael reaction of the chiral lithioenamines derived from α-alkyl β-keto esters and (S)-valine tert-butyl ester is described. Complementary asymmetric syntheses producing either enantiomers from the same ...
WINKLER J D, KIM H S, KIM S, ANDO K, HOUK K N
J. Org. Chem.   62(9) 2957-2962
The application of the tandem Diels-Alder cycloaddition to the stereoselective synthesis of the tricyclic ring system of the taxane diterpenes is described. The exceedingly direct, two-step synthesis of the B/C cis-fused taxane nucleus in 50% over...
Kaori Ando, Tomohiro Wada, Miho Okumura, Hiroshi Sumida
Organic Letters   17 6026-6029
© 2015 American Chemical Society. New Peterson reagents were prepared by introducing alkyloxy groups on the silicon atom in order to fix the conformation of the sulfone anion. The reagents 1d and 1e reacted with a variety of aldehydes after the tr...
Kaori Ando, Kaori Ando, Kevin R. Condroski, Kevin R. Condroski, K. N. Houk, Yun Dong Wu, Sylvie Kim Ly, L. E. Overman
Journal of Organic Chemistry   63 3196-3203
The selectivities of nucleophilic additions of ethyl, vinyl, and ethynyllithium and Grignard reagents to a 2-(3′-phenylpropyl)cycloheptanone were investigated experimentally. In all cases, cis-cycloheptanol was formed preferentially (40:1-6:1). Th...
Hideaki Yamamichi, Shiro Matsukawa, Shiro Matsukawa, Satoshi Kojima, Kaori Ando, Yohsuke Yamamoto
Heteroatom Chemistry   22 553-561
Neutral hexacoordinate organoantimony compounds LSb(Xyl)C 6H 4 (o-Y) [L = tridentate ligand; Xyl = C 6H 3 (3,5-Me 2); Y = CH 2 OMe (4), CH 2 NMe 2 (5), and 2-pyridyl (6)] with intramolecular coordination were synthesized. Single crystal X-ray crys...
Natsuhisa Oka, Kousuke Ito, Futoshi Tomita, Kaori Ando
Chemistry Letters   41 1630-1632
We developed a straightforward and cost-effective method for the synthesis of 2-pyridylphosphinate derivatives based on a nucleophilic aromatic substitution of N-methoxypyridinium salts. The method proved to be useful for synthesizing various 2-py...
Hironori Miyauchi, Shunsuke Chiba, Koji Fukamizu, Kaori Ando, Koichi Narasaka
Tetrahedron   63 5940-5953
Vinylic halides having alcohol, sulfonamide, active methine, and thiol moieties as nucleophiles cyclize to hetero- and carbocycles by intramolecular nucleophilic substitution at the sp2 carbon centers. The density functional theory calculations su...
Natsuhisa Oka, Yasuhiro Morita, Yuta Itakura, Kaori Ando
Chemical Communications   49 11503-11505
Inosine derivatives bearing a phosphodiester group at the O 6-position of the nucleobase were synthesized via phosphitylation of the carbonyl oxygen using phosphoramidites activated by non-nucleophilic acidic activators. © 2013 The Royal Society o...
Natsuhisa Oka, Yuji Takayama, Kaori Ando, Takeshi Wada
Bioorganic and Medicinal Chemistry Letters   22 4571-4574
We developed a method to convert a nucleoside 5′-H-boranophosphonate monoester into the corresponding nucleoside 5′-boranophosphorothioate monoester through temporary protection of the H-boranophosphonate monoester moiety as a diester with 9-fluor...
ANDO K, KITAMURA M, MIURA K, NARASAKA K
Organic Letters   6(14) 2461-2463
(Equation Presented) The intramolecular in-plane SN2 type reaction of haloalkene E-8a was predicted to be a facile process for the first time by DFT calculations (B3LYP/6-31+G(d),SCRF(dipole, solvent = DMF)) (ΔG = 14.4 kcal/mol). The prediction wa...
Theoretical Studies and General Purpose Force Field for the Prediction of Nucleophilic Addition Stereoselectivities
J. Org. Chem.   63 3196-3203   1998年
ANDO K
J. Org. Chem.   69(12) 4203-4209
The nucleophilic 5-endo-trigonal cyclization of 1,1-difluoro-1-alkenes has been studied at the B3LYP/6-31+G(d) level in an Onsager continuum model for DMF. The reaction takes an addition-elimination path. Both the transition-state structures and t...
Kaori Ando
Journal of Organic Chemistry   71 1837-1850
Transition structures for the lithium-bromine exchange reaction of 1,1-dibromoalkenes with methyllithium have been located by both the B3LYP and the MP2 levels of theory with the 6-31+G* basis set. The reaction with methyllithium dimer gave simila...
Masaaki yoshifuji, Ichiro Shima, Kaori Ando, Naoki Inamoto
Tetrahedron Letters   24 933-936
2,3-Dihydro-1H-phosphindole derivatives were obtained from thermal reactions of (2,4,6-tri-tert-butylphenyl)phosphonous dichloride in refluxing toluene, probably through cyclization involving phosphorus radicals with an adjacent methyl of o-tert-b...
Kiyoshi Nagase, Kaori Ando-Nagase, Hiroshi Endoh
Anesthesia and Analgesia   95 1127-1128
ANDO K, GREEN N S, LI Y, HOUK K N
J. Am. Chem. Soc.   121(22) 5334-5335
Kaori Ando
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   72 890-898   2014年1月
Utilization of ab initio and DFT calculations for the development of organic synthesis is described here. The first topic is the base-mediated intramolecular amination of bromoallens having an axial chirality. The treatment of both (4S,aR)- and (4...
Kaori Ando
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   58 869-876
The Horner-Wadsworth-Emmons modification of the Wittig reaction is a widely used method for the preparation of α,β-unsaturated esters. The phosphonate anions are strongly nucleophilic and react readily with carbonyl compounds under mild conditions...
ANDO K
J. Org. Chem.   63(23) 8411-8416
New Horner-Wadsworth-Emmons reagents, ethyl 2- (diarylphosphono)propionates (2), ethyl 2-(diarylphosphono)hexanoates (3), and ethyl 2-(diarylphosphono)-3-methylbutanoates (4) were prepared by alkylation of ethyl (diarylphosphono)acetates. The reac...
Kaori Ando, Kaori Sato
Tetrahedron Letters   52 1284-1287
The Z-selective intramolecular Horner-Wadsworth-Emmons reaction of the substrates 7-12 (RO) 2P(O)CHR′CO 2Et (R′ = (CH 2) nCHO) (R = Ph or o-tBuC 6H 4) gives the 13-18-membered cyclic alkenes selectively (up to Z:E = 97:3) in good yields using NaH ...
Kaori Ando, Kenji Narumiya, Hirokazu Takada, Taiji Teruya
Organic Letters   12 1460-1463
(Figure Presented) When the substrates (ArO)2P(O)CH 2CO2⋯CHO (Ar = Ph, o-tBuPh) were added to a THF solution containing 3 equiv of NaH at 0 °C or Nal DBU at rt over 1-10 h, the intramolecular Horner-Wadsworth-Emmons reaction proceeded efficiently ...
Natsuhisa Oka, Rin Kajino, Kaoru Takeuchi, Haruna Nagakawa, Kaori Ando
Journal of Organic Chemistry   79 7656-7664
Ribofuranosylation of a variety of alcohols with ribofuranosyl iodides in the presence of a base and triphenylphosphine oxide afforded the corresponding α-ribofuranosides with diastereoselectivities ≥ 99:1. This reaction can be carried out under m...
ホルナー・エモンズ反応の反応機構の解明と立体選択的α,β-不飽和エステル類合成への応用
薬学研究の進歩:研究成果報告   17号p.15-23    2001年
安藤香織 Ζ選択的Horner-Wadsworth-Emmons試薬の開発
有機合成化学協会誌(特集号:今、若手研究者はなにを目指しているか)   59(5) 418-419   2001年
理論計算から始まる有機合成への挑戦
化学と工業   57 931-932   2004年

書籍等出版物

 
My Favorite organic Synthesis
The Soiety of Synthetic Organic Chemistry, Japan   2002年   
Ghiron、Thomas著、奈良坂紘一、┣DB安藤香織(/)┫DB訳 演習有機合成化学
東京化学同人   2000年   
有機薬科学実験講座第2巻「創薬化学の基礎となる不斉反応」 第6章エナミン、イミン、ヒドラゾン、オキサゾリンを用いる不斉合成
広川書店   1998年   

競争的資金等の研究課題

 
文部科学省: 
研究期間: 1998年 - 1998年    代表者: 安藤 香織
ジアリールホスホノ酢酸エチルをアルキル化した後、ホルナーエモンズ反応を行えば3置換オレフィンの合成が可能である。本研究ではメチル基、n-ブチル基、i-プロピル基で置換された試薬を合成しそれらの選択性を調べた。ジフェニルホスホノ酢酸エチルの場合アルキル化はDMSO中NaHまたはt-BuOKを用いて行い、収率はメチル体66%、n-ブチル体77%、i-プロビル体68%であった。これらと種々のタイプのアルデヒドとの反応を行った。メチル体試薬については、trans-ヘキセナールとの反応を除くと95%...
文部科学省: 科学研究費補助金(新学術領域研究(研究領域提案型))
研究期間: 2015年 - 2016年    代表者: 安藤 香織
文部科学省: 科学研究費補助金(基盤研究(C))
研究期間: 2013年 - 2015年    代表者: 安藤 香織
Julia-Kocienski反応はテトラゾリルスルホンとアルデヒドからトランス‐アルケンを与える反応で最近生理活性物質の合成によく用いられているが低収率あるいは低選択性となる場合も多い。そこで一般性のたかい合成法の開発を目指してテトラゾイルスルホンの1位のフェニル基を小さな電子供与基メチルに置き換えた試薬の開発を行った。得られた試薬の反応では収率の向上が見られたが、選択性についてはほぼ同様で、改善の余地があった。そこで1位の置換基をさらに小さくしたらどうなるかに興味を持ち、1位に置換基を...
文部科学省: 科学研究費補助金(新学術領域研究(研究領域提案型))
研究期間: 2013年 - 2014年    代表者: 安藤 香織
文部科学省: 科学研究費補助金(新学術領域研究(研究領域提案型))
研究期間: 2013年 - 2014年    代表者: 安藤 香織
茶谷らはRu3(CO)12触媒を用いる脂肪族C-H結合の活性化による2-ピリジルメチルピバロイルアミド(1)のβ位選択的カルボニル化反応を報告している。我々は本反応の反応機構に興味を持ち、触媒の初期構造としてRu単核錯体Aを用いた分子軌道計算による解析を行った。結果は昨年度の報告書で報告し、現在論文執筆準備中である。茶谷らは触媒活性種についての知見を得るため、化学量論量の(1)とRu3(CO)12をトルエン中160℃で加熱して2核錯体Bを得、X線構造解析を行っている。錯体Bの各Ru原子は基...

特許

 
新規アルキル(ジアリール)ホスホノアセテート
特願平9-106532

社会貢献活動

 
講演会講師
【】  京都大学  京都大学  2014年4月18日 - 2014年4月18日