Taku Kitanosono

J-GLOBAL         Last updated: Aug 30, 2019 at 17:45
 
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Name
Taku Kitanosono
E-mail
tkitanosonochem.s.u-tokyo.ac.jp
Section
Faculty of Science
Research funding number
50755981
ORCID ID
0000-0003-0743-1420

Research Areas

 
 

Academic & Professional Experience

 
Apr 2018
 - 
Today
Assistant Professor, School of Science, The University of Tokyo
 
Apr 2015
 - 
Mar 2018
Assistant Professor, School of Science, The University of Tokyo
 

Education

 
Apr 2012
 - 
Mar 2015
Ph.D. Course, Graduate School of Science, The University of Tokyo
 
Apr 2010
 - 
Mar 2012
M.Sc. Course, Graduate School of Science, The University of Tokyo
 

Published Papers

 
Kitanosono Taku, Sakai Masaru, Zhu Lei, Kobayashi Shu
CHEMISTRY LETTERS   48(8) 783-786   Aug 2019   [Refereed]
The use of a chiral copper(II) complex combined with surfactant enabled a tandem nucleophilic addition/protonation sequence of α-branched enones in water. Optically active α-methyl-β-amino ketones were obtained with up to 82% ee. The involvement o...
Kitanosono Taku, Cho Soo Min, Kobayashi Shu
TETRAHEDRON      Oct 2018   [Refereed]
The use of negatively charged aluminosilicate layers and Lewis acidic cations embedded therein allowed efficient cyclocondensation of bisamines with water-soluble aldehydes to be achieved in water. The protocol does not involve acidic or reflux co...
Kitanosono Taku, Xu Pengyu, Kobayashi Shu
SCIENCE   362(6412) 311-315   Oct 2018   [Refereed]
The development of highly reactive and stereoselective catalytic systems is required not only to improve existing synthetic methods but also to invent distinct chemical reactions. Herein, a homogenized combination of nickel-based Lewis acid–surfac...
Yamashita Yasuhiro, Yasukawa Tomohiro, Yoo Woo-Jin, Kitanosono Taku, Kobayashi Shu
CHEMICAL SOCIETY REVIEWS   47(12) 4388-4480   Jun 2018   [Refereed]
Recent developments in catalytic asymmetric aldol reactions have been summarized. Enantioselective aldol reactions are important methods to synthesize β-hydroxy carbonyl compounds in optical pure form, and as such, numerous successful chiral catal...
Kitanosono Taku, Tani Shinki, Kobayashi Shu
ASIAN JOURNAL OF ORGANIC CHEMISTRY   7(2) 350-354   Feb 2018   [Refereed]
A methylene group inserted between proximal carbonyl groups underwent exclusive oxyfunctionalization with sodium chlorite in the presence of redox‐inert HfIV in water. Direct oxidation methods have conventionally suffered from manifold side reacti...
Kitanosono Taku, Masuda Koichiro, Xu Pengyu, Kobayashi Shu
CHEMICAL REVIEWS   118(2) 679-746   Jan 2018   [Refereed]
Traditional organic synthesis relies heavily on organic solvents for a multitude of tasks, including dissolving the components and facilitating chemical reactions, because many reagents and reactive species are incompatible or immiscible with wate...
Isegawa Miho, Sameera W. M. C., Sharma Akhilesh K., Kitanosono Taku, Kato Masako, Kobayashi Shu, Morokuma Keiji
ACS CATALYSIS   7(8) 5370-5380   Aug 2017   [Refereed]
We present a mechanistic survey on the LCu-catalyzed (L = chiral 2,2′-bipyridine ligand) enantioselective boron conjugate addition reaction, carried out using density functional theory (DFT) and artificial force induced reaction (AFIR) methods. Th...
Kitanosono Taku, Kobayashi Shu
In Book "Chiral Lewis Acids in Organic Synthesis" Ed. by J. Mlynarski   299-344   Jun 2017
This chapter highlights the water‐compatible chiral Lewis acid catalysts that emphasize their usefulness and potential application in next‐generation organic synthesis and may result in the development of novel modes of chemical transformations. L...
Kitanosono Taku, Miyo Masumi, Kobayashi Shu
ACS SUSTAINABLE CHEMISTRY & ENGINEERING   4(11) 6101-6106   Nov 2016   [Refereed]
The electrophilic palladation of indoles through C–H bond functionalization with the aid of surfactant was achieved in water in a highly enantioselective manner. The system displayed attractive features that are reminiscent of both precious-metal ...
Liu Zhe, Lebrun Vincent, Kitanosono Taku, Mallin Hendrik, Kohler Valentin, Haussinger Daniel, Hilvert Donald, Kobayashi Shu, Ward Thomas R.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   55(38) 11587-11590   Sep 2016   [Refereed]
Regulation of enzymatic activity is vital to living organisms. Here, we report the development and the genetic optimization of an artificial zymogen requiring the action of a natural protease to upregulate its latent asymmetric transfer hydrogenas...
Kitanosono Taku, Zhu Lei, Liu Chang, Xu Pengyu, Kobayashi Shu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   137(49) 15422-15425   Dec 2015   [Refereed]
Acicular purplish crystals were obtained from Cu(acac)2 and a chiral bipyridine ligand. Although the crystals were not soluble, they nevertheless catalyzed asymmetric silyl conjugate addition of lipophilic substrates in water. Indeed, the reaction...
Zhu Lei, Kitanosono Taku, Xu Pengyu, Kobayashi Shu
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY   11 2007-2011   Oct 2015   [Refereed]
The promising performance of copper(II) complexes was demonstrated for asymmetric boron conjugate addition to α,β-unsaturated nitriles in water. The catalyst system, which consisted of Cu(OAc)2 and a chiral 2,2′-bipyridine ligand, enabled β-boryla...
Kitanosono Taku, Miyo Masumi, Kobayashi Shu
TETRAHEDRON   71(40) 7739-7744   Oct 2015   [Refereed]
The utility of electrophilic palladium(II) species was demonstrated for C–H bond functionalization of indoles and pyrroles in water. The system displayed attractive features that are reminiscent of both precious-metal catalysis and micellar cataly...
Sameera W. M. C., Hatanaka Miho, Kitanosono Taku, Kobayashi Shu, Morokuma Keiji
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   137(34) 11085-11094   Sep 2015   [Refereed]
Density functional theory (DFT), combined with the artificial force-induced reaction (AFIR) method, is used to establish the mechanism of the aqueous Mukaiyama aldol reactions catalyzed by a chiral Fe(II) complex. On the bases of the calculations,...
Kitanosono Taku, Kobayashi Shu
CHEMISTRY-AN ASIAN JOURNAL   10(1) 133-138   Jan 2015   [Refereed]
Enzymes exhibit overwhelmingly superior catalysis compared with artificial catalysts. Current strategies to rival enzymatic catalysis require unmodified or minimally modified structures of active sites, gigantic molecular weight, and sometimes the...
Zhu Lei, Kitanosono Taku, Xu Pengyu, Kobayashi Shu
CHEMICAL COMMUNICATIONS   51(58) 11685-11688   2015   [Refereed]
Cu(I)-based chemistry has flourished over the last decade because of the reliable use of species such as soft acids. However, the unique nature of Cu(II) catalysts allows the well-documented Cu(I)-based chemistry to be extended. Prominent advantag...
Kitanosono Taku, Xu Pengyu, Isshiki Satoshi, Zhu Lei, Kobayashi Shu
CHEMICAL COMMUNICATIONS   50(66) 9336-9339   Aug 2014   [Refereed]
Enantioselective conjugate addition of bis(pinacolato)diboron to α,β-unsaturated imines proceeds smoothly in water in the presence of a chiral copper(II) complex consisting of Cu(OAc)2 and chiral 2,2′-bipyridine. The corresponding β-boryl imines, ...
Kitanosono Taku, Kobayashi Shu
CHEMICAL RECORD   14(1) 130-143   Feb 2014   [Refereed]
Since the discovery of the Mukaiyama aldol reaction in 1973, tremendous efforts have been made to develop a definitive catalyst that catalyzes asymmetric Mukaiyama aldol reactions under mild conditions with broad substrate tolerance. Forty years l...
Kitanosono Taku, Xu Pengyu, Kobayashi Shu
CHEMISTRY-AN ASIAN JOURNAL   9(1) 179-188   Jan 2014   [Refereed]
We have developed CuII‐catalyzed enantioselective conjugate‐addition reactions of boron to α,β‐unsaturated carbonyl compounds and α,β,γ,δ‐unsaturated carbonyl compounds in water. In contrast to the previously reported CuI catalysis that required o...
Kitanosono Taku, Ollevier Thierry, Kobayashi Shu
CHEMISTRY-AN ASIAN JOURNAL   8(12) 3051-3062   Dec 2013   [Refereed]
We have developed asymmetric Mukaiyama aldol reactions of silicon enolates with aldehydes catalyzed by chiral FeII and BiIII complexes. Although previous reactions often required relatively harsh conditions, such as strictly anhydrous conditions, ...
Kitanosono Taku, Kobayashi Shu
ADVANCED SYNTHESIS & CATALYSIS   355(16) 3095-3118   Nov 2013   [Refereed]
Mukaiyama aldol reactions in aqueous media have been surveyed. While the original Mukaiyama aldol reactions entailed stoichiometric use of Lewis acids in organic solvents under strictly anhydrous conditions, Mukaiyama aldol reactions in aqueous me...
Kitanosono Taku, Kobayashi Shu
ASIAN JOURNAL OF ORGANIC CHEMISTRY   2(11) 961-966   Nov 2013   [Refereed]
The use of copper(0) powder in water enables chiral induction as well as high catalytic activity. Water plays a prominent role to determine both the catalytic activity and enantioselection. Elevated temperature is indispensable for the regular rea...
Kitanosono Taku, Xu Pengyu, Kobayashi Shu
CHEMICAL COMMUNICATIONS   49(74) 8184-8186   2013   [Refereed]
It was proved that a judicious choice of counteranion played a prominent role in Cu(II) catalysis for enantioselective boron conjugate additions in water; the use of Cu(OH)2 renders heterogeneous catalysis, whereas Cu(OAc)2 renders homogeneous cat...
Kobayashi Shu, Ueno Masaharu, Kitanosono Taku
BISMUTH-MEDIATED ORGANIC REACTIONS   311 1-17   2012   [Refereed]
Several bismuth-catalyzed synthetic reactions, which proceed well in aqueous media, are discussed. Due to increasing demand of water as a solvent in organic synthesis, catalysts that can be used in aqueous media are becoming more and more importan...
Kitanosono Taku, Sakai Masaru, Ueno Masaharu, Kobayashi Shu
ORGANIC & BIOMOLECULAR CHEMISTRY   10(35) 7134-7147   2012   [Refereed]
Asymmetric Michael reactions and enantioselective protonations between enones and thiols were catalyzed by a Sc(OTf)3–chiral 2,2′-bipyridine complex in water. The remarkable governing of the enantioselectivity for simple introduction of protons de...
Kobayashi Shu, Xu Pengyu, Endo Toshimitsu, Ueno Masaharu, Kitanosono Taku
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   51(51) 12763-12766   2012   [Refereed]
The enantioselective 1,4‐addition of diboron to α,β‐unsaturated compounds proceeds smoothly in the presence of catalytic amounts of Cu(OH)2 and chiral 2,2′‐bipyridine ligand in water. A wide substrate scope of α,β‐unsaturated carbonyl compounds, i...
Mukherjee Chandan, Kitanosono Taku, Kobayashi Shu
CHEMISTRY-AN ASIAN JOURNAL   6(9) 2308-2311   Sep 2011   [Refereed]
The kinetics of chiral scandium(III)‐catalyzed hydroxymethylation of silicon enolates using aqueous formaldehyde have been investigated, and a reaction mechanism of this process in organic/aqueous medium is proposed.
Ueno Masaharu, Kitanosono Taku, Sakai Masaru, Kobayashi Shu
ORGANIC & BIOMOLECULAR CHEMISTRY   9(10) 3619-3621   2011   [Refereed]
Asymmetric Michael reactions of thiols with enones were catalyzed by a Sc(OTf)3–chiral bipyridine complex at room temperature in water without using any organic solvents, to afford the desired sulfides in high yields with high enantioselectivities.
Kobayashi Shu, Kitanosono Taku, Ueno Masaharu
SYNLETT   (13) 2033-2036   Aug 2010   [Refereed]
Metal-hydroxide-catalyzed addition reactions of hydrazonoester with allenylboronate in aqueous media are described. The propargyl adduct was obtained selectively by using copper(II) hydroxide, whereas the allenyl adduct was produced preferentially...

Books etc

 
Water-Compatible Chiral Lewis Acids
Kitanosono Taku, Kobayashi Shu
Wiley-VCH   Jun 2017   ISBN:3527341293
This chapter highlights the water‐compatible chiral Lewis acid catalysts that emphasize their usefulness and potential application in next‐generation organic synthesis and may result in the development of novel modes of chemical transformations. L...
00210 The Aldol reaction: group IV enolates (Mukaiyama, Enol Ethers)
Kobayashi Shu, Yamashita Yasuhiro, Yoo Woo –Jin, Kitanosono Taku, Soulé Jean‐François
in Comprehensive Organic Synthesis (2nd Edition), Elsevier   Dec 2014   
Aldol reactions are among the most important carbon–carbon bond-forming reactions. Compared with commonly utilized enolates derived from group I and II elements, enolates based on group IV elements, such as silicon and tin, are relatively stable a...

Teaching Experience

 
 

Research Grants & Projects

 
Project Year: Apr 2019 - Mar 2021    Investigator(s): Taku Kitanosono
Japan Society for Promotion of Sciences: Grant-in-Aid for Early-Career Scientists
Project Year: Apr 2018 - Mar 2020    Investigator(s): Taku Kitanosono
Japan Society for Promotion of Sciences: Grant-in-Aid for Research Activity start-up
Project Year: Aug 2015 - Mar 2017    Investigator(s): Taku Kitanosono
Japan Society for Promotion of Sciences: Grant-in-Aid for JSPS Fellows
Project Year: Apr 2013 - Mar 2015    Investigator(s): Taku Kitanosono