Preparation of 2-alkenylperhydro-1,3-benzoxazines and application for 2-isoxazolines synthesis

被引：1

作者：

Poisson, Carl ^{[1
]}

Lacoste, Jean-Eric ^{[1
]}

Rochon, Fernande D. ^{[1
]}

Breau, Livain ^{[1
]}

机构：

[1] Univ Quebec, Dept Chim, Montreal, PQ H3C 3P8, Canada

来源：

TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 21期

基金：

加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION; NITRILE OXIDE CYCLOADDITIONS; POLYKETIDE BUILDING-BLOCKS; RADICAL CYCLIZATION; REGIOSELECTIVITY; GRIGNARD; OLEFINS; SUGAR; ACIDS;

D O I：

10.1016/j.tetasy.2009.10.033

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Various 2-substituted-N-benzyl-4,4,7-trimethyl-trans-octahydro-1,3-benzoxazines 2 were prepared from the condensation of (-)-8-benzylaminomenthol 1 derived from (+)-pulegone, with acrolein, crotonaldehyde, cinnamaldehyde, 2(E)-N,N-diisopropyl-4-oxobut-2-enamide, ethyl (2E)-4-oxobut-2-enoate, and 2-furaldehyde in 71-96% yield. The 1,3-dipolar cycloaddition with aceto- and benzonitrile oxide gave the corresponding 2-isoxazoline cycloadducts. The origin of the stereoselectivity (4'S, 5'S-cycloadducts up to 64% de) arises from the cycloaddition of the dipole to the top of the Re,Re-alkene face of dipolarophile 2. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2447 / 2461

页数：15

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