A simple and efficient asymmetric synthesis of 3-alkyl-isoindolin-1-ones

被引：55

作者：

Pérard-Viret, J

Prangé, T

Tomas, A

Royer, J

机构：

[1] Univ Paris 05, CNRS, UMR 8638, Fac Pharm,Lab Chim Therapeut, F-75270 Paris 06, France

[2] Univ Paris 05, CNRS, UMR 8015, Fac Pharm,Lab Cristallog, F-75006 Paris, France

来源：

TETRAHEDRON | 2002年 / 58卷 / 25期

关键词：

isoindolin-1-one; alkylation; carbanions; (R)-phenylglycinol; amide bases;

D O I：

10.1016/S0040-4020(02)00462-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple asymmetric access to 3-alkyl-isoindolin-1-ones was investigated through the diastereoselective alkylation of 2-[(1R)-2-hydroxy- 1-phenylethyl]-2,3-dihydro-1H-isoindolin-1-one 5. High diastereoselectivities were observed with LDA or LiHMDS while the isolated yields were modest (about 50%). In contrast the use of NaHMDS gave good isolated yields (up to 85%) but lowered diastereoselectivities. This methodology offers an efficient asymmetric synthesis of 3-alkylated isoindolin-1-ones. (C) 2002 Elsevier Science Ltd. All rights reserved.

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收藏

页码：5103 / 5108

页数：6

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