P (PhCH2NCH2CH2) 3N Catalysis of Mukaiyama Aldol Reactions of Aliphatic, Aromatic, and Heterocyclic Aldehydes and Trifluoromethyl Phenyl Ketone

VR Chintareddy, K Wadhwa…

Index: Chintareddy, Venkat Reddy; Wadhwa, Kuldeep; Verkade, John G. Journal of Organic Chemistry, 2009 , vol. 74, # 21 p. 8118 - 8132

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Citation Number: 40

Abstract

Herein we find that proazaphosphatrane 1c is a very efficient catalyst for Mukaiyama aldol reactions of aldehydes with trimethylsilyl enolates in THF solvent. Only the activated ketone 2, 2, 2-trifluoroacetophenone underwent clean aldol product formation with a variety of trimethylsilyl enolates under similar conditions as the aldehydes. The reactions were carried out at room temperature using (1-methoxy-2-methyl-1-propenyloxy) trimethylsilane, ...