Organic letters

A catalytic asymmetric vinylogous mukaiyama aldol reaction

LV Heumann, GE Keck

Index: Heumann, Lars V.; Keck, Gary E. Organic Letters, 2007 , vol. 9, # 21 p. 4275 - 4278

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Citation Number: 34

Abstract

We investigated the use of this direct method employing diene 4 (Scheme 1). Although preliminary experiments using this reagent afforded good yields in additions to aldehydes using BF 3 ·OEt 2 as Lewis acid, the use of reagent 4 in catalytic asymmetric additions using BITIP catalysis was not promising. Reactions using this reagent were far more sluggish than typical allylation reactions using this catalyst, and yields were lower. Aliphatic aldehydes required extended reaction ...