The synthesis of enantiomerically pure disubstituted aziridines and N-alkoxy aziridines

被引:28
作者
Hanessian, S [1 ]
Cantin, LD [1 ]
机构
[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada
关键词
D O I
10.1016/S0040-4039(99)02211-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The addition of a chloroallyl phosphonamide anion to oximes has allowed the preparation of a variety of cis-disubstituted N-alkoxy aziridines in enantiomerically pure form. Oxidative cleavage of the chiral auxiliary followed by derivatization of the products has allowed the preparation of enantiopure N-alkoxy aziridines. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:787 / 790
页数:4
相关论文
共 37 条
[1]   HYDROGENATION OF 1-BENZYL-3-(2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)-AZIRIDINE-2-CARBOXYLIC ACID ETHYL-ESTER [J].
AMBROSI, HD ;
DUCZEK, W ;
RAMM, M ;
JAHNISCH, K .
TETRAHEDRON LETTERS, 1994, 35 (41) :7613-7616
[2]   Stereoselective synthesis of erythro beta-substituted aspartates [J].
Antolini, L ;
Bucciarelli, M ;
Caselli, E ;
Davoli, P ;
Forni, A ;
Moretti, I ;
Prati, F ;
Torre, G .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) :8784-8789
[3]  
BACKER HJ, 1950, RECL TRAV CHIM PAY B, V69, P1223
[4]   Aziridine-allylsilane-mediated total synthesis of (-)-yohimbane [J].
Bergmeier, SC ;
Seth, PP .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3237-3243
[5]  
Boises E., 1985, U.S. Pat., Patent No. [4,517,183, 4517183]
[6]  
Brois S. J., 1970, J AM CHEM SOC, V92, P1079
[7]   REACTION OF 1-(HALOMETHYL)BICYCLO[1.1.1]PENTANES WITH STRONG BASES - EVIDENCE FOR A CARBENE-BRIDGEHEAD OLEFIN-CARBENE REARRANGEMENT [J].
BUNZ, U ;
HERPICH, W ;
PODLECH, J ;
POLBORN, K ;
PRATZEL, A ;
STEPHENSON, DS ;
SZEIMIES, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7637-7641
[8]   Asymmetric aziridine synthesis via aza-Darzens reaction of bromoacylcamphorsultam [J].
Cantrill, AA ;
Hall, LD ;
Jarvis, AN ;
Osborn, HMI ;
Raphy, J ;
Sweeney, JB .
CHEMICAL COMMUNICATIONS, 1996, (23) :2631-2632
[9]   Stereoselective synthesis of quaternary α-amino acids.: Part 1:: Acyclic compounds [J].
Cativiela, C ;
Diaz-de-Villegas, MD .
TETRAHEDRON-ASYMMETRY, 1998, 9 (20) :3517-3599
[10]   REACTIVITY OF 2,3-AZIRIDINO-2,3-DIDEOXY-D-LYXONO-GAMMA-LACTONE DERIVATIVES, RIGID ANALOGS OF AZIRIDINE-2-CARBOXYLIC ESTERS, TOWARD SOFT AND HARD NUCLEOPHILES - CONTROL OF LACTONE VS AZIRIDINE RING-OPENING AND C-2 VS C-3 REGIOSELECTIVITY [J].
DAUBAN, P ;
DUBOIS, L ;
DAU, METH ;
DODD, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :2035-2043