3-(N,N-diacylamino)quinazolin-4(3H)-ones as enantioselective acylating agents for amines

被引：30

作者：

Al-Sehemi, AG ^{[1
]}

Atkinson, RS ^{[1
]}

Fawcett, J ^{[1
]}

Russell, DR ^{[1
]}

机构：

[1] Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(00)00138-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The presence of an N-N chiral axis in a 3-(N-benzoyl-N-isobutanoyl)aminoquinazolin-4(3H)-one (DAQ) bearing a chiral substituent in the 2-position of the quinazolinone allows separation of two enantiopure diastereoisomers; one of these diastereoisomers reacts with racemic 2-methylpiperidine to give (R)(+)-1-benzoyl-2-methylpiperidine (95% ee) and (S)-2-methylpiperidine (91% ee) even using stoichiometric quantities of reagents (1 equiv. DAQ: 2 equiv. amine). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2239 / 2242

页数：4

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