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Highly Enantioselective Synthesis of α-Trifluoromethyldihydropyrans Using a Chiral Trifluoroethyl-substituted Thiourea Catalyst Derived from Amino Acid

✍ Scribed by Peng Li; Gang Zhao; Shizheng Zhu

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 151 KB
Volume: 29
Category: Article
ISSN: 0256-7660
DOI: 10.1002/cjoc.201100034

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✦ Synopsis

Abstract

An enantioselective Michael addition of ethyl 4,4,4‐trifluoro‐3‐oxobutanoate to α,β‐unsaturated ketone esters using a chiral alkyl‐substituted thiourea catalyst is reported. Excellent levels of stereo‐induction (up to 98% ee) under mild reaction conditions were obtained to afford the corresponding α‐trifluoromethyldihydropyrans.

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