Asymmetric Diels-Alder addition of cyclopentadiene to chiral naphthoquinones

被引：15

作者：

Brimble, MA ^{[1
]}

McEwan, JF ^{[1
]}

Turner, P ^{[1
]}

机构：

[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 07期

基金：

澳大利亚研究理事会;

关键词：

D O I：

10.1016/S0957-4166(98)00087-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Diels-Alder reactions of 1,4-naphthoquinones bearing a chiral auxiliary at C-2, with cyclopentadiene under Lewis acid conditions afforded the corresponding Diels-Alder. adducts. High levels of diastereomeric excess were obtained using (R)-pantolactone, (S)-N-methyl-2-hydroxysuccinimide and trans-2-phenylcyclohexanol as auxiliaries. Moderate asymmetric induction was achieved using Oppolzer's camphorsultam and (R)-(+)-4-benzyl-2-oxazolidinone as auxiliaries. X-Ray crystallographic analysis of the pantolactone adduct enabled determination of the stereochemistry of all adducts obtained. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1239 / 1255

页数：17

共 23 条

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