An asymmetric approach to pyrrolidinone and pyrrolizidinone systems by intramolecular oxime-olefin cycloaddition

被引:33
作者
Chiacchio, U
Corsaro, A
Pistara, V
Rescifina, A
Romeo, G
Romeo, R
机构
[1] UNIV MESSINA,DIPARTIMENTO FARMACOCHIM,I-98168 MESSINA,ITALY
[2] UNIV ARCAVACATA,DIPARTIMENTO CHIM,I-87036 ARCAVACATA,ITALY
关键词
D O I
10.1016/0040-4020(96)00358-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Homochiral functionalized pyrrolidinone and pyrrolizidinone systems have been achieved by stereoselective intramolecular oxime-olefin cycloaddition starting from homochiral amino acids, and by subsequent reduction of the obtained fused isoxazolidines. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:7875 / 7884
页数:10
相关论文
共 42 条
[1]  
ANNUNZIATA R, 1989, GAZZ CHIM ITAL, V119, P253
[2]   SYNTHESIS OF HOMOCHIRAL 3-OXA-2,7-DIAZABICYCLO[3.3.0]OCTANES FROM AMINO-ACIDS BY INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION OF NITRONES [J].
AURICH, HG ;
FRENZEN, G ;
GENTES, C .
CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (03) :787-795
[3]  
AURICH HG, 1991, CHEM BER, V124, P2329
[4]   HIGHLY DIASTEREOSELECTIVE FORMATION OF BICYCLIC COMPOUNDS BY INTRAMOLECULAR CYCLOADDITION OF CHIRAL THIAALKENYL NITRONES [J].
AURICH, HG ;
QUINTERO, JLR .
TETRAHEDRON, 1994, 50 (13) :3929-3942
[5]   EFFECT OF NITROGEN SUBSTITUTION ON THE DIASTEREOSELECTION OF INTRAMOLECULAR NITRONE ALKENE CYCLOADDITIONS [J].
BALDWIN, SW ;
GEDON, SC .
SYNTHETIC COMMUNICATIONS, 1991, 21 (04) :587-596
[6]   DIASTEREOSELECTIVITY IN THE INTRAMOLECULAR CYCLOADDITION REACTIONS OF NITRONES DERIVED FROM 5-ALKENALS AND CHIRAL HYDROXYLAMINES [J].
BALDWIN, SW ;
MCFADYEN, RB ;
AUBE, J ;
WILSON, JD .
TETRAHEDRON LETTERS, 1991, 32 (35) :4431-4434
[7]   CARBOCYCLIC COMPOUNDS FROM MONOSACCHARIDES .1. TRANSFORMATIONS IN THE GLUCOSE SERIES [J].
BERNET, B ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1979, 62 (06) :1990-2016
[8]  
BUEMI G, 1993, HETEROCYCLES, V36, P2005
[9]  
CARRUTHERS V, 1990, TETRAHEDRON ORGANIC, V8, P269
[10]   STEREOSELECTIVE APPROACHES TO BIOACTIVE CARBOHYDRATES AND ALKALOIDS - WITH A FOCUS ON RECENT SYNTHESES DRAWING FROM THE CHIRAL POOL [J].
CASIRAGHI, G ;
ZANARDI, F ;
RASSU, G ;
SPANU, P .
CHEMICAL REVIEWS, 1995, 95 (06) :1677-1716