ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR STEREOSELECTIVE SYNTHESES OF PYRROLIDINE AND PYRROLIZIDINE SYSTEMS

被引：36

作者：

CHIACCHIO, U ^{[1
]}

CASUSCELLI, F ^{[1
]}

CORSARO, A ^{[1
]}

LIBRANDO, V ^{[1
]}

RESCIFINA, A ^{[1
]}

ROMEO, R ^{[1
]}

ROMEO, G ^{[1
]}

机构：

[1] UNIV MESSINA,DIPARTIMENTO FARMACOCHIM,I-98168 MESSINA,ITALY

来源：

TETRAHEDRON | 1995年 / 51卷 / 19期

关键词：

D O I：

10.1016/0040-4020(95)00233-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Homochiral functionalized pyrrolidine and pyrrolizidine systems have been achieved by stereoselective intramolecular 1,3-dipolar cycloaddition of homochiral nitrones, starting from homochiral amino acids, and by subsequent reduction of the obtained cycloadducts.

引用

收藏

页码：5689 / 5700

页数：12

相关论文

共 27 条

[11] STEREOSELECTIVE SYNTHESIS OF FUSED GAMMA-LACTAMS BY INTRAMOLECULAR NITRONE CYCLOADDITION [J].

CHIACCHIO, U ;

BUEMI, G ;

CASUSCELLI, F ;

PROCOPIO, A ;

RESCIFINA, A ;

ROMEO, R .

TETRAHEDRON, 1994, 50 (18) :5503-5514

[12]

Confalone P. N., 1988, ORG REACTIONS, V36, P1

[13] STEREOSELECTIVE ADDITION OF LITHIOETHYL ACETATE TO BOC-L-PROLINAL - A CONVENIENT CHIRAL SYNTHETIC BUILDING BLOCK FOR THE PYRROLIZIDINE ALKALOID RING-SYSTEM [J].

HANSON, GJ ;

BARAN, JS ;

LINDBERG, T .

TETRAHEDRON LETTERS, 1986, 27 (31) :3577-3580

[14]

HARRIS BD, 1986, HETEROCYCLES, V24, P1045

[15]

HASSNER A, 1991, HETEROCYCLES IN BIO-ORGANIC CHEMISTRY, P130

[16] NEW SYMMETRICAL CHIRAL DIBENZYL-SUBSTITUTED AND DIPHENYL-SUBSTITUTED DIAMIDO-18-CROWN-6, DITHIONOAMIDO-18-CROWN-6, DIAZA-18-CROWN-6, AND AZAPYRIDINO-18-CROWN-6 LIGANDS [J].

HUSZTHY, P ;

OUE, M ;

BRADSHAW, JS ;

ZHU, CY ;

WANG, TM ;

DALLEY, NK ;

CURTIS, JC ;

IZATT, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (20) :5383-5394

[17]

IHARA M, 1988, J CHEM SOC CHEM COMM, V9, P10

[18] INTRAMOLECULAR NITRILE OXIDE CYCLOADDITION (INOC) REACTIONS IN THE INDOLE SERIES .2. TOTAL SYNTHESIS OF RACEMIC AND OPTICALLY-ACTIVE PALICLAVINE AND 5-EPI-PALICLAVINE [J].

KOZIKOWSKI, AP ;

CHEN, YY .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (25) :5248-5250

[19] THE ADDITION OF NITRONES TO OLEFINS - A NEW ROUTE TO ISOXAZOLIDINES [J].

LEBEL, NA ;

WHANG, JJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (23) :6334-6335

[20] SYNTHESIS OF (+/-)-ALLOSEDAMINE BY IODIDE TREATMENT OF ISOXAZOLIDINIUM SALTS [J].

LIGUORI, A ;

OTTANA, R ;

ROMEO, G ;

SINDONA, G ;

UCCELLA, N .

CHEMISCHE BERICHTE, 1989, 122 (10) :2019-2020