N-VINYL AND N-UNSUBSTITUTED BETA-LACTAMS FROM 1-SUBSTITUTED 2-AZA-1,3-BUTADIENES

被引:32
作者
GEORG, GI
HE, P
KANT, J
MUDD, J
机构
[1] Department of Medicinal Chemistry, University of Kansas, Lawrence
基金
美国国家卫生研究院;
关键词
D O I
10.1016/0040-4039(90)87005-K
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of acid chlorides and N-vinyl imines results in the stereoselective formation of cis N-vinyl β-lactams. The N-vinyl protecting group can be removed either oxidatively or hydrolytically to yield N-unsubstituted β-lactams. © 1990.
引用
收藏
页码:451 / 454
页数:4
相关论文
共 14 条
[1]   DIELS-ALDER REACTIONS OF AZADIENES [J].
BOGER, DL .
TETRAHEDRON, 1983, 39 (18) :2869-2939
[2]   SYNTHESIS AND PROPERTIES OF DERIVATIVES OF 2-AZABUTADIENE [J].
BOHME, H ;
INGENDOH, A .
CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (04) :1297-1303
[3]   REAGENTS AND SYNTHETIC METHODS A NOVEL SYNTHETIC APPROACH TO N-UNSUBSTITUTED BETA-LACTAMS [J].
COSSIO, FP ;
PALOMO, C .
TETRAHEDRON LETTERS, 1985, 26 (35) :4235-4238
[4]   2-AZA-1,3-DIENES AS NOVEL PRECURSORS FOR THE SYNTHESIS OF N-UNSUBSTITUTED BETA-LACTAMS - A 3 STEP SYNTHESIS OF 4-ACETOXY-3-PHENOXY-2-AZETIDINONE [J].
GEORG, GI ;
KANT, J ;
HE, P ;
LY, AM ;
LAMPE, L .
TETRAHEDRON LETTERS, 1988, 29 (20) :2409-2412
[5]   ASYMMETRIC-SYNTHESIS OF (1'R,3R,4R)-4-ACETOXY-3-(1'-((TERT-BUTYLDIMETHYLSILYL)OXY)ETHYL)-2-AZETIDINONE AND OTHER 3-(1'-HYDROXYETHYL)-2-AZETIDINONES FROM (S)-(+)-ETHYL 3-HYDROXYBUTANOATE - FORMAL TOTAL SYNTHESIS OF (+)-THIENAMYCIN [J].
GEORG, GI ;
KANT, J ;
GILL, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1129-1135
[6]  
GEORG GI, 1989, STUDIES NATURAL PROD, V4, P431
[7]   SYNTHESIS OF THE CHIRAL SYNTHETIC BUILDING BLOCK (1R,5S)-3-PHENYL-4-OXA-2,6-DIAZABICYCLO[3.2.0]HEPT-2-EN-7-ONE FROM 6-AMINOPENICILLANIC ACID [J].
HABICH, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (09) :711-711
[8]   NUCLEAR ANALOGS OF BETA-LACTAM ANTIBIOTICS .1. THE SYNTHESIS OF 6-BETA-AMIDOCYCLONOCARDICINS [J].
HECK, JV ;
CHRISTENSEN, BG .
TETRAHEDRON LETTERS, 1981, 22 (50) :5027-5030
[9]  
HOLDEN GG, 1982, CHEM BIOL BETA LACTA, V2, pCH2
[10]   FLUORIDE-ION MEDIATED PETERSON ALKENATION OF BIS(TRIMETHYLSILYL)METHYLIMINES - A NOVEL SYNTHESIS OF 2-AZA-1,3-DIENES AND N-VINYL-BETA-LACTAMS [J].
LASARTE, J ;
PALOMO, C ;
PICARD, JP ;
DUNOGUES, J ;
AIZPURUA, JM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (02) :72-74