C(1)-substituted menthol derivatives: Self-removing chiral auxiliaries for asymmetric conjugate additions to cycloalkenones

被引：12

作者：

Funk, RL ^{[1
]}

Yang, G ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 06期

关键词：

D O I：

10.1016/S0040-4039(98)02627-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C(1)-substituted (-)-menthone derivatives 3 were prepared by the stereoselective addition of the alkenyllithium reagents 9 to menthone (8) and subsequent acid catalyzed hydrolysis of the dioxolane protecting groups. Conjugate addition of cuprate reagents to enones 3a,b followed by a methanol quench directly gave the beta-alkylcycloalkanones 7 via retro-aldol reactions in 80-91% ee. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1073 / 1074

页数：2

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