Lewis acid mediated diastereoselective keto-ene cyclization on chiral perhydro-1,3-benzoxazines: synthesis of enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines

被引：18
|
作者：
Andres, Celia [1 ]
Gonzalez, Israel
Nieto, Javier
Roson, Carlos D.
机构：
[1] Univ Valladolid, CINQUIMA, E-47011 Valladolid, Spain
来源：
TETRAHEDRON | 2009年 / 65卷 / 47期
关键词：
Carbonyl-ene cyclization; Chiral; 3-hydroxypyrrolidines; Perhydro-1,3-benzoxazines; Diastereoselective synthesis; Lewis acids; INTRAMOLECULAR CARBONYL ENE; IMDA REACTION; DERIVATIVES; OXIDATION; CATALYSTS; ALCOHOLS; ETHERS; ENTRY;
D O I：
10.1016/j.tet.2009.09.091
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chiral 2-acyl-3-allyl-perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol were easily cyclized in the presence of Lewis acids at 0 degrees C. The diastereoselectivity of the cyclization was dependent on the nature of the Lewis acid. The cyclization compounds can be transformed into enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines by ring opening of the N,O-acetal moiety and subsequent elimination of the menthol appendage. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9728 / 9736
页数：9
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