Synthesis and applications of (1R, 5S,6S)-6-(2,2-dimethylpropanamido)spiro[4.4]nonan-1-ol as a chiral auxiliary in Diels-Alder reactions

被引：22

作者：

Burke, MJ ^{[1
]}

Allan, MM ^{[1
]}

Parvez, M ^{[1
]}

Keay, BA ^{[1
]}

机构：

[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 13期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0957-4166(00)00242-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A short asymmetric synthesis of (1R,5S,6S)-6-(2,2-dimethylpropanamido)spiro[4.4]nonan-1-ol 7 is described along with its application as a chiral auxiliary in various Diels-Alder reactions. The enantioselectivity of the Diels-Alder adducts ranged from 86-98% ee. The Diels-Alder adducts were easily removed from the chiral auxiliary and the latter was recyclized. The absolute and relative stereochemistry of 7 was determined from an X-ray crystal structure of the p-bromobenzoate derivative of 7. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2733 / 2739

页数：7

共 38 条

[1] DIASTEREOSELECTIVE ALKYLATION REACTIONS EMPLOYING A CAMPHOR-BASED CHIRAL OXAZINONE AUXILIARY [J].