(-)-Ephedrine as an auxiliary for the asymmetric synthesis of atropisomeric amides by dynamic resolution under thermodynamic control

被引：51

作者：

Clayden, J ^{[1
]}

Lai, LW ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(01)00416-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N,N-Dialkyl-2-formylbenzamides and N,N-dialkyl-2-formyl-1-naphthamides condense with (-)-ephedrine in refluxing toluene to give oxazolidines both as single diastereoisomers with respect to the new stereogenic centre and as single conformers with respect to the slowly-rotating Ar-CONR2 bond. In the naphthamide series, removal of the ephedrine auxiliary by hydrolysis returns the starting aldehyde (isolated by reduction to the more stable alcohol) in enantiomerically enriched form (up to 94% ee). Overall, the two-step sequence amounts to a dynamic resolution under thermodynamic control. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3163 / 3166

页数：4

共 33 条

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