Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization

被引：69

作者：

Clayden, J ^{[1
]}

Menet, CJ ^{[1
]}

Tchabanenko, K ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2002年 / 58卷 / 23期

关键词：

kainic acid; stereoselective; cyclization; lithium amide; organolithium;

D O I：

10.1016/S0040-4020(02)00379-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral lithium amide bases are able to deprotonate N-benzyl-N-cumyl anisamides enantioselectively to yield enantiomerically enriched benzylic organolithiums. These spontaneously undergo dearomatising cyclisation to yield, in high enantiomeric excess enantiomerically enriched partially saturated isoindolones, which in some cases may be recrystallised to enantiomeric purity. These isoindolone derivatives are converted in nine steps, among them a surprisingly regioselective Baeyer-Villiger reaction, to (-)-kainic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：4727 / 4733

页数：7

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