(R)- or (S)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoic acid as a new chiral auxiliary for solid phase asymmetric Diels-Alder reactions

被引：18

作者：

Akkari, R ^{[1
]}

Calmès, M ^{[1
]}

Escale, F ^{[1
]}

Iapichella, J ^{[1
]}

Rolland, M ^{[1
]}

Martinez, J ^{[1
]}

机构：

[1] Univ Montpellier 2, CNRS, UMR 5810, Lab Aminoacides Peptides & Prot, F-34095 Montpellier 5, France

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 16期

关键词：

D O I：

10.1016/j.tetasy.2004.06.012

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of enantiopure (R)- and (S)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoic acid is described and the corresponding supported chiral acrylate derivative has been used as a dienophile in solid phase asymmetric Diels-Alder reactions with different dienes. In all cases, the reaction gave the expected compound in good yield and with high regio or endo selectivity. Moreover, a high facial diastereoselectivity (86-99% de) was obtained using 2,3-dimethylbutadiene, cyclopentadiene or 1,3-cyclohexadiene. In contrast, low to moderate facial diastereoselectivity (40-76% de) was observed with isoprene depending on the polymer used. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2515 / 2525

页数：11

共 55 条

[1] (S)-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl) acetic acid as a solid supported chiral auxiliary in the asymmetric synthesis of β2-homoarylglycines [J].