Conformational Fixation of Enolates by Intramolecular Metal⊙⊙⊙ Fluorine Interaction

T Yamazaki, M Ando, T Kitazume, T Kubota…

Index: Yamazaki, Takashi; Ando, Makoto; Kitazume, Tomoya; Kubota, Toshio; Omura, Masao Organic Letters, 1999 , vol. 1, # 6 p. 905 - 908

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Citation Number: 28

Abstract

Methyl acetates with fluorine-containing auxiliaries at their 2 position were demonstrated to react smoothly with various electrophiles in a re face preferential manner (up to 90% de). This was interpreted as the result of an intermediary enolate constructing a bicyclo [3.3. 0] system by the concomitant intramolecular chelation of a metal with α-oxygen and fluorine, resulting in the auxiliary effectively blocking attack from the opposite si face.

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