Synthesis of trifluoromethylated compounds with four consecutive asymmetric centers via sequential [3,3]-Ireland-Claisen rearrangement and iodolactonization

被引：30

作者：

Konno, T ^{[1
]}

Kitazume, T ^{[1
]}

机构：

[1] TOKYO INST TECHNOL,DEPT BIOENGN,MIDORI KU,YOKOHAMA,KANAGAWA 226,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 02期

关键词：

D O I：

10.1016/S0957-4166(96)00492-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Iodolactonization and osmylation of enantiomerically pure alpha-methoxy-beta-trifluoromethyl-gamma,delta-unsaturated carboxylic acid derivatives, which were prepared via [3,3]-Ireland-Claisen rearrangement of alpha-methoxyacetic acid (gamma-trifluoromethyl) allylesters, were investigated. The former proceeded in a highly stereoselective manner, and the construction of four successive asymmetric centers was achieved in a high yield. On the other hand, the latter gave the desired gamma-lactone in moderate yield. The mechanism is also discussed by using MOPAC AM1 calculation. (C) 1997 Elsevier Science Ltd.

引用

页码：223 / 230

页数：8

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