ASYMMETRIC-SYNTHESIS OF TRANS AND CIS BETA-LACTAMS

被引：22

作者：

BRAUN, M

SACHA, H

GALLE, D

ELALALI, A

机构：

[1] Institut für Organische Chemie, Makromolekulare Chemie Heinrich-Heine-Universität Düsseldorf

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 24期

关键词：

D O I：

10.1016/0040-4039(95)00772-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The condensation of doubly deprotonated triphenylglycol propionate 4a and imines 1 leads to the formation of trans beta-lactams 5 in a diastereoselective and enantioselective manner (85 to > 97% e.e.). On the other hand, the lithium enolates of the propionates 4b,c, derived from triphenylglycol as well, afford predominantly cis 2-azetidinones 6 in 87 to > 97% e.e.

引用

收藏

页码：4213 / 4216

页数：4

相关论文

共 35 条

[1] STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES BEARING A CHIRAL AUXILIARY [J].

ANNUNZIATA, R ;

BENAGLIA, M ;

CINQUINI, M ;

COZZI, F ;

RAIMONDI, L .

TETRAHEDRON LETTERS, 1993, 34 (43) :6921-6924

[2] ANTI-SELECTIVE AND DIASTEREOFACIALLY SELECTIVE ALDOL REACTIONS WITH (R)-2-SILOXY-1,2,2-TRIPHENYLETHYL PROPIONATE [J].

BRAUN, M ;

SACHA, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (10) :1318-1320

[3] RECENT ADVANCES IN STEREOSELECTIVE ALDOL REACTIONS OF ESTER AND THIOESTER ENOLATES [J].

BRAUN, M ;

SACHA, H .

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1993, 335 (08) :653-668

[4]

BRAUN M, 1991, ANGEW CHEM, V103, P1369

[5]

BRAUN M, 1993, ORG SYNTH, V72, P32

[6] PREPARATION OF 3-AMINO-4-(HYDROXYMETHYL)AZETIDIN-2-ONES FROM THE REACTION OF GLYCINE ENOLATES WITH IMINES OF A GLYCOALDEHYDE [J].

BROWN, MJ ;

OVERMAN, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1933-1936

[7]

BROWN MJ, 1989, HETEROCYCLES, V29, P2225

[8] ASYMMETRIC-SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF CHOLESTEROL ABSORPTION INHIBITOR, SCH-48461 [J].

BURNETT, DA .

TETRAHEDRON LETTERS, 1994, 35 (40) :7339-7342

[9] BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - ENANTIOSELECTIVE SYNTHESIS OF (+)-PS-5 [J].

CAINELLI, G ;

PANUNZIO, M ;

GIACOMINI, D ;

MARTELLI, G ;

SPUNTA, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6879-6880

[10] HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF BETA-AMINO ACID-ESTERS AND BETA-LACTAMS FROM ACHIRAL ESTERS AND IMINES [J].

COREY, EJ ;

DECICCO, CP ;

NEWBOLD, RC .

TETRAHEDRON LETTERS, 1991, 32 (39) :5287-5290

← 1 2 3 4 →