Dynamic resolution of atropisomeric amides using proline-derived imidazolines and ephedrine-derived oxazolidines

被引：50

作者：

Clayden, J ^{[1
]}

Lai, LW ^{[1
]}

Helliwell, M ^{[1
]}

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

来源：

TETRAHEDRON | 2004年 / 60卷 / 20期

关键词：

atropisomeric amides; imidazolines; oxazolidines; ephedrine;

D O I：

10.1016/j.tet.2004.01.101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation of atropisomeric tertiary 2-formyl naphthamides or 2-formyl benzamides with some chiral diamines and amino alcohols leads, via a dynamic resolution process, to single atropisomers of tertiary amides bearing chiral imidazolidines or oxazolidines. Hydrolysis of the new heterocycle competes a dynamic thermodynamic resolution of the starting aldehyde, and rapid reduction allows the isolation of atropisomeric amides bearing 2-hydroxymethyl substituents in enantiomerically enriched form. Evidence that the reactions are under thermodynamic control is presented. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4399 / 4412

页数：14

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