Aziridination of styrene derivatives with 3-acetoxyaminoquinazolinones: probing transition state geometry from changes in diastereoselectivity

被引:13
作者
Atkinson, RS [1 ]
Claxton, TA [1 ]
Lochrie, IST [1 ]
Ulukanli, S [1 ]
机构
[1] Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England
关键词
D O I
10.1016/S0040-4039(98)00939-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In aziridinations of beta-substituted styrenes (4), (5) and (6) with the enantiopure 3-acetoxyaminoquinazolinone (1), diastereoselectivity (dr) increases from 5:1 for 6) to 10:1 (for (10) to similar to 20:1 (for (11)): changes in transition state geometry which account for this increase are rationalised using Frontier;Orbital Theory. (C) 1998 Elsevier Science Ltd. All rights reserved.
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收藏
页码:5113 / 5116
页数:4
相关论文
共 12 条
[1]   AZIRIDINATION OF ELECTRON-RICH ACYCLIC ALLYLIC ALCOHOLS USING 3-ACETOXYAMINOQUINAZOLINONES [J].
ATKINSON, RS ;
FAWCETT, J ;
RUSSELL, DR ;
WILLIAMS, PJ .
TETRAHEDRON LETTERS, 1995, 36 (18) :3241-3244
[2]   Aziridination of alpha,beta-unsaturated esters bearing allylic hydroxy groups with 3-acetoxyaminoquinazolinones: Evidence for a mechanism comprising Michael addition-S(N)2 nucleophilic displacement of acetoxy for aziridination of alpha,beta-unsaturated esters [J].
Atkinson, RS ;
Williams, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (16) :1951-1959
[3]   AZIRIDINATION BY OXIDATIVE ADDITION OF N-AMINOQUINAZOLONES TO ALKENES - EVIDENCE FOR NON-INVOLVEMENT OF N-NITRENES [J].
ATKINSON, RS ;
GRIMSHIRE, MJ ;
KELLY, BJ .
TETRAHEDRON, 1989, 45 (10) :2875-2886
[4]   Desilylative elimination of the quinazolinone ring from 1-(4-oxoquinazolin-3-yl)-2-silylaziridines; Preparation of an N-H aziridine in high enantiomeric excess by in situ nucleophilic addition to the derived azirine [J].
Atkinson, RS ;
Coogan, MP ;
Lochrie, IST .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (06) :897-900
[5]   AZIRIDINATION OF CYCLOHEX-2-ENOLS AND 3-SUBSTITUTED CYCLOHEXENES - COMPARISON WITH EPOXIDATION [J].
ATKINSON, RS ;
KELLY, BJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08) :1515-1519
[6]   Reagent-controlled diastereoselectivity in aziridination of alkenes by chiral 3-acetoxyamino-3,4-dihydroquinazolin-4-ones: 1'-(t-butyldimethylsilyloxy)ethyl as the chiral 2-substituent on the quinazolinone [J].
Atkinson, RS ;
Coogan, MP ;
Lochrie, IST .
TETRAHEDRON LETTERS, 1996, 37 (29) :5179-5182
[7]  
ATKINSON RS, 1996, J CHEM SOC CHEM COMM, P1935
[8]  
HENBEST HB, 1957, J CHEM SOC, P1985
[9]  
Sheldrick GM., 1993, SHELXL 93 PROGRAM CR, DOI DOI 10.1107/S2053229614026540
[10]  
SHELDRICK GM, 1991, SHELXTL PC RELEASE 4