Synthesis of α-methyl kainic acid by stereospecific lithiation-dearomatizing cyclization of a chiral benzamide

被引：31

作者：

Clayden, J ^{[1
]}

Knowles, FE ^{[1
]}

Menet, CJ ^{[1
]}

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 16期

关键词：

D O I：

10.1016/S0040-4039(03)00570-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereospecific lithiation of N-alpha-methylbenzyl benzamides gives configurationally stable tertiary benzyllithiums which undergo a stereospecific dearomatizing cyclization with >99% retention of stereochemistry. The products are partially saturated isoindolinones which carry a new fully-substituted stereogenic centre. A ten-step sequence converts one of these products to the alpha-methyl analogue of kainic acid. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：3397 / 3400

页数：4

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