Stereoselective synthesis of 2-hydroxymorpholines and aminodiols via a three-component boro-Mannich reaction

被引：29

作者：

Berrée, F

Debache, A

Marsac, Y

Collet, B

Girard-Le Bleiz, P

Carboni, B

机构：

[1] Univ Rennes 1, CNRS, UMR 6226, F-35042 Rennes, France

[2] Univ Constantine, Inst Chim, Constantine 25000, Algeria

来源：

TETRAHEDRON | 2006年 / 62卷 / 17期

关键词：

2-hydroxymorpholine; multicomponent reaction; boro-Mannich condensation; boronic acid; chiral aminodiol;

D O I：

10.1016/j.tet.2006.02.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The three-component coupling of an 1,2-aminoalcohol, a 1,2-dicarbonyl compound and a boronic acid was investigated. The reaction is supposed to proceed through the formation of a heterocyclic iminium species followed by the addition of the organoboron derivative. The diastereoselectivity of this process is discussed. Best results were observed when the probable intermediate was generated from a preformed 3-phenylthiomorpholin-2-ol. Products of this three-component boro-Mannich could be readily converted to the corresponding aminodiols by reduction with lithium aluminium hydride. (c) 2006 Elsevier Ltd. All rights reserved.

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页码：4027 / 4037

页数：11

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