Tetrahedron

A new route to α-fluorovinylphosphonates utilizing Peterson olefination methodology

R Waschbüsch, J Carran, P Savignac

Index: Waschbuesch, Rachel; Carran, John; Savignac, Philippe Tetrahedron, 1996 , vol. 52, # 45 p. 14199 - 14216

Full Text: HTML

Citation Number: 39

Abstract

Several α-fluorovinylphosphonates (6) have been synthesised from the Peterson olefination reaction applied to both aldehydes and ketones in conjunction with α-lithiated-α-fluoro-α- trimethylsilylmethylphosphonate (2). The reaction with aldehydes gives mainly the E-isomer whereas reaction with ketones gives mainly the Z-isomer. We propose a closed transition state to explain the results of our study.