3-di-[(S)-2-acetoxypropanoyl] aminoquinazolin-4(3H)-ones:: stereostructure and application in kinetic resolution of amines

被引：11

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)00139-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Whereas 3-diacylaminoquinazolin-4(3H)-ones (DAQs) have been previously shown to undergo rapid exo/endo-endo/exo conformational interconversion of their imide carbonyl groups, the title DAQs are believed to exist in one single exo/endo form and consequently their N-N bonds are chiral axis: one of these DAQs, substituted with a diphenylmethyl group on the Q-2 position, reacts preferentially with one enantiomer of racemic 2-methyl-piperidine at the 2-acetoxypropanoyl imide carbonyl group (ee 94%). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2243 / 2246

页数：4

共 3 条

[1] 3-(N,N-diacylamino)quinazolin-4(3H)-ones as enantioselective acylating agents for amines [J].

Al-Sehemi, AG ;

Atkinson, RS ;

Fawcett, J ;

Russell, DR .

TETRAHEDRON LETTERS, 2000, 41 (13) :2239-2242

[2] The N-N bond as a chiral axis: 3-Diacylaminoquinazolinones as chiral acylating agents [J].

Atkinson, RS ;

Barker, E ;

Edwards, PJ ;

Thomson, GA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (10) :1047-1055

[3]

ATKINSON RS, 1996, J CHEM SOC CHEM COMM, P1051

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