ASYMMETRIC-SYNTHESIS OF 1,3,4-TRISUBSTITUTED AND 3,4-DISUBSTITUTED 2-AZETIDINONES - STRATEGY BASED ON USE OF D-GLUCOSAMINE AS A CHIRAL AUXILIARY IN THE STAUDINGER REACTION

被引：43

作者：

BARTON, DHR

GATEAUOLESKER, A

ANAYAMATEOS, J

CLEOPHAX, J

GERO, SD

CHIARONI, A

RICHE, C

机构：

[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE

[2] TEXAS A&M UNIV SYST,DEPT CHEM,COLLEGE STN,TX 77843

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 11期

关键词：

D O I：

10.1039/p19900003211

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient asymmetric approach to the synthesis of trisubstituted azetidin-2-ones is presented. The strategy relies on the use of ketene-imine cycloaddition between ketenes generated from phthalimidoacetic and methoxyacetic acids and a chiral Schiff base (3) derived from 3,4;5,6-di-Oisopropylidene-D- glucosamine propane dithioacetal (2) and cinnamaldehyde; the removal of the chiral auxiliary group by β-elimination is a noteworthy facet of this communication.

引用

页码：3211 / 3212

页数：2

共 13 条

[1] AN ENANTIOSELECTIVE SYNTHESIS OF LORACARBEF (LY163892/KT3777) [J].

BODUROW, CC ;

BOYER, BD ;

BRENNAN, J ;

BUNNELL, CA ;

BURKS, JE ;

CARR, MA ;

DOECKE, CW ;

ECKRICH, TM ;

FISHER, JW ;

GARDNER, JP ;

GRAVES, BJ ;

HINES, P ;

HOYING, RC ;

JACKSON, BG ;

KINNICK, MD ;

KOCHERT, CD ;

LEWIS, JS ;

LUKE, WD ;

MOORE, LL ;

MORIN, JM ;

NIST, RL ;

PRATHER, DE ;

SPARKS, DL ;

VLADUCHICK, WC .

TETRAHEDRON LETTERS, 1989, 30 (18) :2321-2324

[2] MONOCYCLIC BETA-LACTAM ANTIBIOTICS [J].

CIMARUSTI, CM ;

SYKES, RB .

MEDICINAL RESEARCH REVIEWS, 1984, 4 (01) :1-24

[3] RECENT DEVELOPMENTS IN THE FIELD OF BETA-LACTAM ANTIBIOTICS [J].

DURCKHEIMER, W ;

BLUMBACH, J ;

LATTRELL, R ;

SCHEUNEMANN, KH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (03) :180-202

[4] THE ASYMMETRIC-SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .5. APPLICATION OF CHIRAL ALPHA,BETA-EPOXYIMINES IN KETENE-IMINE CYCLO-ADDITION REACTIONS LEADING TO HOMOCHIRAL 3-AMINOAZETIDINONES [J].

EVANS, DA ;

WILLIAMS, JM .

TETRAHEDRON LETTERS, 1988, 29 (40) :5065-5068

[5] A NOVEL RING-CLOSURE STRATEGY FOR THE CARBAPENEMS - THE TOTAL SYNTHESIS OF (+)-THIENAMYCIN [J].

HANESSIAN, S ;

DESILETS, D ;

BENNANI, YL .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3098-3103

[6]

HUBSCHWERLEN C, 1984, HELV CHIM ACTA, V4, P1

[7] STEREOSPECIFIC CONSTRUCTIONS OF CHIRAL BETA-LACTAMS [J].

LABIA, R ;

MORIN, C .

JOURNAL OF ANTIBIOTICS, 1984, 37 (10) :1103-1129

[8] A NOVEL SYNTHESIS OF THE MONOBACTAM ANTIBIOTIC CARUMONAM [J].

MANCHAND, PS ;

LUK, KC ;

BELICA, PS ;

CHOUDHRY, SC ;

WEI, CC ;

SOUKUP, M .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5507-5512

[9] CYCLO-ADDITIONS OF CYANOKETENES TO CINNAMYLIDENEAMINES AND BENZYLIDENEAMINES - SYNTHETIC SCOPE, STEREOCHEMISTRY, AND MECHANISM [J].

MOORE, HW ;

HUGHES, G ;

SRINIVASACHAR, K ;

FERNANDEZ, M ;

NGUYEN, NV ;

SCHOON, D ;

TRANNE, A .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (22) :4231-4238

[10]

Morin R. B., 1982, CHEM BIOL BETA LACTA, V1-3

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