Asymmetric Michael Reaction of α‑CF3 Thioester and α,β-Unsaturated Aldehyde Catalyzed by Diphenylprolinol Silyl Ether

Asymmetric Michael reaction of α-CF3 thioester and α,β-unsaturated aldehyde is catalyzed by diphenylprolinol silyl ether to afford the trifluoromethyl substituted Michael product with excellent enantioselectivity. Although the Michael products were generated as a mixture of syn- and anti-isomers, th...

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Bibliographic Details
Published in:Organic letters 2019-07, Vol.21 (13), p.5183-5186
Main Authors: Hayashi, Yujiro, Yamada, Tomoaki, Sato, Misaki, Watanabe, Shoya, Kwon, Eunsang, Iwasaki, Kotaro, Umemiya, Shigenobu
Format: Article
Language:English
Online Access:Get full text
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Summary:Asymmetric Michael reaction of α-CF3 thioester and α,β-unsaturated aldehyde is catalyzed by diphenylprolinol silyl ether to afford the trifluoromethyl substituted Michael product with excellent enantioselectivity. Although the Michael products were generated as a mixture of syn- and anti-isomers, they can be transformed to single isomers of other useful compounds, such as lactone, lactam, piperidine, dihydropyran containing trifluoromethyl groups, or fluoro substituents.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01774