Conformational fixation of enolates by intramolecular metal•••fluorine interaction

被引：33

作者：

Yamazaki, T

Ando, M

Kitazume, T

Kubota, T

Omura, M

机构：

[1] Tokyo Inst Technol, Dept Bioengn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

[2] Ibaraki Univ, Dept Mat Sci, Hitachi, Ibaraki 3168511, Japan

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 06期

关键词：

D O I：

10.1021/ol990821c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] 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 alpha-oxygen and fluorine, resulting in the auxiliary effectively blocking attack from the opposite si face.

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收藏

页码：905 / 908

页数：4

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