Meisenheimer rearrangements of N-allyl 2-azabornane derivatives

被引:19
作者
Buston, JEH
Coldham, I
Mulholland, KR
机构
[1] Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England
[2] SmithKline Beecham Pharmaceut, Harlow CM19 5AW, Essex, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 16期
关键词
D O I
10.1039/a903050f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A study of the asymmetric [2,3]-Meisenheimer rearrangement of tertiary amine-N-oxides was carried out, in order to provide a method for the preparation of chiral allylic alcohols. The use of 2-azabornane as a chiral auxiliary gives rise to chiral tertiary amine-N-oxides, which undergo the [2,3]-Meisenheimer rearrangement with high levels of stereoselectivity. Reductive N,O-bond cleavage, mediated by ultrasound, of the O-allyl-hydroxylamine allows access to the chiral allylic alcohol.
引用
收藏
页码:2327 / 2334
页数:8
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