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Asymmetric Organocatalytic Cascade Michael/Hemiketalization/Retro‐Aldol Reaction of 2‐[( E )‐2‐Nitrovinyl]phenols with 2,4‐Dioxo‐4‐arylbutanoates: A Convenient Access to Chiral α‐Keto Esters
Author(s) -
Liu Yunting,
Wang Youming,
Song Haibin,
Zhou Zhenghong,
Tang Chuchi
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300552
Subject(s) - squaramide , chemistry , enantioselective synthesis , bifunctional , aldol reaction , phenols , organocatalysis , michael reaction , organic chemistry , catalysis , stereochemistry
An unprecedented organocatalytic enantioselective cascade Michael/hemiketalization/retro‐aldol reaction of 2‐[( E )‐2‐nitrovinyl]phenols and 2,4‐dioxo‐4‐arylbutanoates is described. With a bifunctional squaramide catalyst incorporating (1 R ,2 R )‐1,2‐diphenylethane‐1,2‐diamine, the reactions afford products in 75–99% yields with 80–98% ee . This process provides an enantioselective pathway for the synthesis of chiral α‐keto esters, precursors of 3‐arylproline derivatives, δ‐amino α‐keto acids or cyclic α‐keto lactams.