Enzymatic resolution of N-arylaziridine carboxylates

被引:11
作者
Kumar, HMS [1 ]
Rao, MS [1 ]
Chakravarthy, PP [1 ]
Yadav, JS [1 ]
机构
[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1016/j.tetasy.2003.10.027
中图分类号
O61 [无机化学];
学科分类号
070301 [无机化学]; 081704 [应用化学];
摘要
N-Arylaziridine-2-carboxylates have been enzymatically resolved using the lipase from Candida rugosa to afford optically active aziridine carboxylates in moderate to high enantiomeric purity. The absolute configuration of the unknown aziridine carboxylates was assigned as S by chemical correlation. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:127 / 130
页数:4
相关论文
共 23 条
[1]
Asymmetric synthesis of N-aryl aziridines [J].
Aires-de-Sousa, J ;
Prabhakar, S ;
Lobo, AM ;
Rosa, AM ;
Gomes, MJS ;
Corvo, MC ;
Williams, DJ ;
White, AJP .
TETRAHEDRON-ASYMMETRY, 2002, 12 (24) :3349-3365
[2]
A VERSATILE SYNTHESIS OF STEREOSPECIFICALLY LABELED D-AMINO ACIDS AND RELATED ENZYME-INHIBITORS [J].
AXELSSON, BS ;
OTOOLE, KJ ;
SPENCER, PA ;
YOUNG, DW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (16) :1085-1086
[3]
NUCLEOPHILIC RING-OPENING OF AZIRIDINE-2-CARBOXYLATES WITH WITTIG REAGENTS - AN ENANTIOEFFICIENT SYNTHESIS OF UNSATURATED AMINO-ACIDS [J].
BALDWIN, JE ;
ADLINGTON, RM ;
ROBINSON, NG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) :153-155
[4]
NON-PROTEINOGENIC AMINO-ACID SYNTHESIS - THE BETA-ANION DERIVED FROM ASPARTIC-ACID, AND ITS APPLICATION TO ALPHA-AMINO-ACID SYNTHESIS [J].
BALDWIN, JE ;
MOLONEY, MG ;
NORTH, M .
TETRAHEDRON, 1989, 45 (19) :6309-6318
[5]
ENZYMATIC RESOLUTION OF AZIRIDINE-CARBOXYLATES [J].
BUCCIARELLI, M ;
FORNI, A ;
MORETTI, I ;
PRATI, F ;
TORRE, G .
TETRAHEDRON-ASYMMETRY, 1993, 4 (05) :903-906
[6]
CANDIDA-CYLINDRACEA LIPASE-CATALYZED HYDROLYSIS OF METHYL AZIRIDINE-2-CARBOXYLATES AND AZIRIDINE-2,3-DICARBOXYLATES [J].
BUCCIARELLI, M ;
FORNI, A ;
MORETTI, I ;
PRATI, F ;
TORRE, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (23) :3041-3045
[7]
BURGER KK, 1999, TETRAHEDRON-ASYMMETR, V10, P679
[8]
Enantioselectivity of alcohol-treated Candida rugosa lipase in the kinetic resolution of racemic methyl 2-aryloxypropionates in water and aqueous organic media [J].
Cipiciani, A ;
Bellezza, F ;
Fringuelli, F ;
Stillitano, M .
TETRAHEDRON-ASYMMETRY, 1999, 10 (23) :4599-4605
[9]
FURUKAWA N, 1976, SYNTHESIS-STUTTGART, P30
[10]
HANESSIAN S, 1992, SYNLETT, P33