Zinc-mediated asymmetric epoxidation of nitro alkenes with oxygen

被引:31
作者
Enders, D [1 ]
Kramps, L [1 ]
Zhu, JQ [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
D O I
10.1016/S0957-4166(98)00424-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The asymmetric epoxidation of nitro alkenes using oxygen in the presence of diethylzinc and N-methyl pseudoephedrine as a chiral additive is reported. This method provides an access to 3-substituted trans-2-nitro oxiranes of excellent diastereomeric purity (de greater than or equal to 98%) and with medium to good enantiomeric excesses (ee=36-82%). (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3959 / 3962
页数:4
相关论文
共 8 条
[1]   PREPARATION OF ALPHA-SUBSTITUTED S-PHENYLTHIO ESTERS FROM 2-NITRO-2-PHENYLTHIO OXIRANES [J].
ASHWELL, M ;
JACKSON, RFW ;
KIRK, JM .
TETRAHEDRON, 1990, 46 (21) :7429-7442
[2]   SYNTHETIC ENZYMES .4. HIGHLY ENANTIOSELECTIVE EPOXIDATION BY MEANS OF POLYAMINOACIDS IN A TRIPHASE SYSTEM - INFLUENCE OF STRUCTURAL VARIATIONS WITHIN THE CATALYSTS [J].
COLONNA, S ;
MOLINARI, H ;
BANFI, S ;
JULIA, S ;
MASANA, J ;
ALVAREZ, A .
TETRAHEDRON, 1983, 39 (09) :1635-1641
[3]   Asymmetric epoxidation of enones with oxygen in the presence of diethylzinc and (R,R)-N-methylpseudoephedrine [J].
Enders, D ;
Zhu, JQ ;
Raabe, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15) :1725-1728
[4]  
Enders D, 1997, LIEBIGS ANN-RECL, P1101
[5]   A NEW APPROACH TO THE SYNTHESIS OF BETA-HYDROXY-ALPHA-AMINO ACIDS USING (ARYLTHIO)NITROOXIRANES [J].
JACKSON, RFW ;
PALMER, NJ ;
WYTHES, MJ ;
CLEGG, W ;
ELSEGOOD, MRJ .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) :6431-6440
[6]   SYNTHETIC ENZYMES .2. CATALYTIC ASYMMETRIC EPOXIDATION BY MEANS OF POLYAMINO-ACIDS IN A TRIPHASE SYSTEM [J].
JULIA, S ;
GUIXER, J ;
MASANA, J ;
ROCAS, J ;
COLONNA, S ;
ANNUZIATA, R ;
MOLINARI, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (06) :1317-1324
[7]  
SOKOLOV NA, 1972, ZH ORG KHIM+, V8, P2371
[8]   CHEMISTRY OF NITRO COMPOUNDS .5. CHEMISTRY OF ALPHA-NITROEPOXIDES - SYNTHESIS OF USEFUL INTERMEDIATES VIA NUCLEOPHILIC RING-OPENING OF ALPHA-NITROEPOXIDES [J].
VANKAR, YD ;
SHAH, K ;
BAWA, A ;
SINGH, SP .
TETRAHEDRON, 1991, 47 (42) :8883-8906