ENANTIOSPECIFIC AND DIASTEREOSELECTIVE SYNTHESIS OF 4,4-DISUBSTITUTED-3-AMINO-2-AZETIDINONES, STARTING FROM D-SERINE

被引：48

作者：

AGENO, G

BANFI, L

CASCIO, G

GUANTI, G

MANGHISI, E

RIVA, R

ROCCA, V

机构：

[1] IST CHIM ORGAN, I-16132 GENOA, ITALY

[2] CNR, CTR STUDIO CHIM COMPOSTI CICLOALIFATICI & AROMAT, I-16132 GENOA, ITALY

[3] LUSO FARMACO SPA, I-20132 MILAN, ITALY

来源：

TETRAHEDRON | 1995年 / 51卷 / 29期

关键词：

D O I：

10.1016/0040-4020(95)00427-A

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A strategy for the preparation of 4,4-disubstituted-3-amino-2-azetidinones which are useful intermediates for the synthesis of analogues of monosulfactam Tigemonam, was developed. It employs D-serine as chiral starting material and involves, as key steps, the diastereoselective addition of organometal compounds to ketones 9 and the stereospecific cyclization of tertiary alcohols 7 to the beta-lactams 6.

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页码：8121 / 8134

页数：14

相关论文

共 60 条

[1]

Anelli P. L., 1990, ORG SYNTH, V69, P212

[2] OXIDATION OF DIOLS WITH ALKALI HYPOCHLORITES CATALYZED BY OXAMMONIUM SALTS UNDER 2-PHASE CONDITIONS [J].

ANELLI, PL ;

BANFI, S ;

MONTANARI, F ;

QUICI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2970-2972

[3]

ANELLI PL, 1987, J ORG CHEM, V52, P2559

[4] CHEMOENZYMATIC PREPARATION OF A KEY INTERMEDIATE FOR CARBAPENEM SYNTHESIS STARTING FROM ASYMMETRIZED BIS(HYDROXYMETHYL)ACETALDEHYDE (BHYMA-ASTERISK) [J].

BANFI, L ;

GUANTI, G ;

NARISANO, E .

TETRAHEDRON, 1993, 49 (33) :7385-7392

[5] HIGHLY REGIOSELECTIVE AND DIASTEREOSELECTIVE FRIEDEL-CRAFTS ALKYLATION OF PHENOLS WITH ALPHA-AMINO ALDEHYDES - SYNTHESIS OF OPTICALLY-ACTIVE EPHEDRINE-LIKE COMPOUNDS [J].

BIGI, F ;

CASNATI, G ;

SARTORI, G ;

ARALDI, G ;

BOCELLI, G .

TETRAHEDRON LETTERS, 1989, 30 (09) :1121-1124

[6] SYNTHESIS OF A CHIRAL SERINE ALDEHYDE EQUIVALENT AND ITS CONVERSION TO CHIRAL ALPHA-AMINO-ACID DERIVATIVES [J].

BLASKOVICH, MA ;

LAJOIE, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5021-5030

[7] THE CHEMISTRY OF THE TRITERPENES AND RELATED COMPOUNDS .18. ELUCIDATION OF THE STRUCTURE OF POLYPORENIC ACID-C [J].

BOWERS, A ;

HALSALL, TG ;

JONES, ERH ;

LEMIN, AJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1953, (SEP) :2548-2560

[8] DESICCANT EFFICIENCY IN SOLVENT DRYING .3. DIPOLAR APROTIC-SOLVENTS [J].

BURFIELD, DR ;

SMITHERS, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20) :3966-3968

[9] DESICCANT EFFICIENCY IN SOLVENT DRYING - REAPPRAISAL BY APPLICATION OF A NOVEL METHOD FOR SOLVENT WATER ASSAY [J].

BURFIELD, DR ;

LEE, KH ;

SMITHERS, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (18) :3060-3065

[10] STEREOCONTROLLED ONE-POT CONVERSIONS OF ALPHA-ALKOXY ESTERS TO SYN-1,2-DIOL AND ANTI-1,2-DIOL DERIVATIVES [J].

BURKE, SD ;

DEATON, DN ;

OLSEN, RJ ;

ARMISTEAD, DM ;

BLOUGH, BE .

TETRAHEDRON LETTERS, 1987, 28 (34) :3905-3906

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