The first generation and stereospecific alkylation of α-trifluoromethyl oxiranyl anion

被引:36
作者
Yamauchi, Y [1 ]
Katagiri, T [1 ]
Uneyama, K [1 ]
机构
[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan
关键词
D O I
10.1021/ol016829f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Generation and reactions of oxiranyl anion 2 stabilized by a trifluoromethyl group are described. Treatment of (S)-2,3-epoxy-1,1,1-trifluoropropane (75% ee) with n-BuLi followed by electrophiles gave corresponding 2-alkylated epoxide 3 with retention of stereochemistry in moderate to good yields. The reaction is applicable for a general synthesis of optically active trifluoromethylated tertiary alcohols.
引用
收藏
页码:173 / 176
页数:4
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