2005年1月
Enantio- and diastereoselective Michael reaction of 1,3-dicarbonyl compounds to nitroolefins catalyzed by a bifunctional thiourea
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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- 巻
- 127
- 号
- 1
- 開始ページ
- 119
- 終了ページ
- 125
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/ja044370p
- 出版者・発行元
- AMER CHEMICAL SOC
We synthesized a new class of bifunctional catalysts bearing a thiourea moiety and an amino group on a chiral scaffold. Among them, thiourea le bearing 3,5-bis(trifluoromethyl) benzene and dimethylamino groups was revealed to be highly efficient for the asymmetric Michael reaction of 1,3-dicarbonyl compounds to nitroolefins. Furthermore, we have developed a new synthetic route for (R)-(-)-baclofen and a chiral quaternary carbon center with high enantioselectivity by Michael reaction. In these reactions, we assumed that a thiourea moiety and an amino group of the catalyst activates a nitroolefin and a 1,3-dicarbonyl compound, respectively, to afford the Michael adduct with high enantio- and diastereoselectivity.
- リンク情報
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- DOI
- https://doi.org/10.1021/ja044370p
- J-GLOBAL
- https://jglobal.jst.go.jp/detail?JGLOBAL_ID=200902233645587690
- PubMed
- https://www.ncbi.nlm.nih.gov/pubmed/15631461
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000226240900042&DestApp=WOS_CPL
- ID情報
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- DOI : 10.1021/ja044370p
- ISSN : 0002-7863
- J-Global ID : 200902233645587690
- PubMed ID : 15631461
- Web of Science ID : WOS:000226240900042