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Enantioselective Mukaiyama-Aldol Reaction of Pyruvates and 1-Phenyl- 1-trimethylsilyloxyethene Catalyzed by Lanthanide/Pybox Complexes

✍ Scribed by Giovanni Desimoni; Giuseppe Faita; Francesca Piccinini; Marco Toscanini

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 96 KB
Volume: 2006
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200600716

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✦ Synopsis

Abstract

The enantioselective Mukaiyama‐aldol reaction between 1‐phenyl‐1‐trimethylsilyloxyethene (1) and three pyruvates (2a–c) is catalyzed by the lanthanide triflate complexes of(4__S__,5__S__)‐2,6‐bis[5‐phenyl‐4‐(triisopropylsilyloxy)methyl‐1,3‐oxazolin‐2‐yl]pyridine (3). The best catalysts are the Lu^III^‐ and Sc^III^‐based complexes that give high yields of (S)‐4a–c and enantiomeric excesses up to 99.5 %. The La^III^‐based complex favors the formation of the opposite enantiomer [77 % ee of (R)‐4c]. The rationale of the stereochemical outcome is proposed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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