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A General Asymmetric Aldol Reaction of Silyl Ketene Acetals Derived from Simple Esters to Aryl α‐Keto Esters
Author(s) -
Le Engers Julie,
Pagenkopf Brian L.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901086
Subject(s) - chemistry , ketene , oxazoline , silylation , aldol reaction , enantioselective synthesis , aryl , steric effects , organic chemistry , yield (engineering) , thio , catalysis , alkyl , materials science , metallurgy
A general method for the enantioselective addition of O , O ‐ketene silyl acetals made from simple esters to α‐keto esters catalyzed by a CuCl 2 · bis(oxazoline) complex is reported that overcomes the limitations of the classic aldol reaction, such as steric intolerance and the need for expensive thio esters. This method excels with aryl α‐keto esters and provides products in good yield and high ee that are not readily available by alternative strategies. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)