Organic letters

Bis (2, 2, 2-trifluoroethyl) bromophosphonoacetate, a novel HWE reagent for the preparation of (E)-α-bromoacrylates: A general and stereoselective method for the …

K Tago, H Kogen

Index: Tago, Keiko; Kogen, Hiroshi Organic Letters, 2000 , vol. 2, # 13 p. 1975 - 1978

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Citation Number: 46

Abstract

A novel reagent, methyl bis (2, 2, 2-trifluoroethoxy) bromophosphonoacetate (3a), was designed and prepared in order to efficiently synthesize (E)-α-bromoacrylates, which are useful precursors for various CC bond formations. Honer-Wadsworth-Emmons (HWE) reaction of various aldehydes with 3a in the presence of t-BuOK and 18-C-6 gave the corresponding (E)-α-bromoacrylate derivatives with high stereoselectivity. Using the (E)-α- ...