FACTORS THAT CAUSE CONTRASTERIC ALKYLATION OF A CYCLOPENTANE-1,2-DICARBOXYLIC ACID MONOESTER

被引：11

作者：

KIGOSHI, H ^{[1
]}

IMAMURA, Y ^{[1
]}

YOSHIKAWA, K ^{[1
]}

NIWA, H ^{[1
]}

YAMADA, K ^{[1
]}

机构：

[1] NAGOYA UNIV,FAC SCI,DEPT CHEM,NAGOYA,AICHI 464,JAPAN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 35期

关键词：

D O I：

10.1016/0040-4039(91)80034-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereochemical outcome in the alkylation of the enolate generated from a cyclopentane-1,2-dicarboxylic acid monoester is described. The alkylation of the Li enolate with an alkylating reagent having a hard leaving group such as Cl gave a contrasteric alkylation (alkylation from the more hindered side of the enolate) product, predominantly. An important factor effecting contrasteric alkylation was found to be complexation of the hard leaving group of the alkylating reagent to the carboxylate Li counterion in the enolate.

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页码：4541 / 4544

页数：4

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