BETA-LACTAM FORMATION VIA RHODIUM(II) CATALYZED CARBON-HYDROGEN INSERTION REACTIONS OF ALPHA-DIAZO AMIDES

被引：14

作者：

DOYLE, MP

OON, SM

VANDERHEIDE, FR

BROWN, CB

机构：

[1] Department of Chemistry, Trinity University, San Antonio

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1993年 / 3卷 / 11期

关键词：

D O I：

10.1016/S0960-894X(01)80966-5

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Diazoacetoacetamides undergo rhodium(II) catalyzed decomposition to form beta-lactam products in high yield and with exceptional stereocontrol. Diazoacetamides generally yield mixtures of beta- and gamma-lactam products whose preference for beta-lactam formation can be enhanced by rhodium(II) 2-phenoxybenzoate. Dirhodium(II) catalysts with chiral carboxamide ligands afford a new enantioselective route to lactams.

引用

收藏

页码：2409 / 2414

页数：6

相关论文

共 33 条

[1] RHODIUM (II) CATALYZED-REACTIONS OF DIAZO-CARBONYL COMPOUNDS [J].

ADAMS, J ;

SPERO, DM .

TETRAHEDRON, 1991, 47 (10-11) :1765-1808

[2] RHODIUM ACETATE CATALYZES THE ADDITION OF CARBENOIDS ALPHA-OXYGENS TO ETHER OXYGENS [J].

ADAMS, J ;

POUPART, MA ;

GRENIER, L ;

SCHALLER, C ;

OUIMET, N ;

FRENETTE, R .

TETRAHEDRON LETTERS, 1989, 30 (14) :1749-1752

[3] A STEREOCONTROLLED ROUTE TO OPTICALLY-ACTIVE 1-METHYL CARBAPENEMS [J].

BROWN, P ;

SOUTHGATE, R .

TETRAHEDRON LETTERS, 1986, 27 (02) :247-250

[4] TOTAL SYNTHESIS OF A NUCLEAR ANALOGUE OF PENICILLIN-CEPHALOSPORIN ANTIBIOTICS [J].

BRUNWIN, DM ;

LOWE, G ;

PARKER, J .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (15) :865-&

[5] A NEW SYNTHETIC APPROACH TO PENICILLINS [J].

COREY, EJ ;

FELIX, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (11) :2518-&

[6] CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].

DOYLE, MP .

CHEMICAL REVIEWS, 1986, 86 (05) :919-939

[7] CONSTRUCTION OF BETA-LACTAMS BY HIGHLY SELECTIVE INTRAMOLECULAR C-H INSERTION FROM RHODIUM(II) CARBOXYLATE CATALYZED-REACTIONS OF DIAZOACETAMIDES [J].

DOYLE, MP ;

SHANKLIN, MS ;

OON, SM ;

PHO, HQ ;

VANDERHEIDE, FR ;

VEAL, WR .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3384-3386

[8] CONFORMATIONAL AND ELECTRONIC PREFERENCES IN RHODIUM(II) CARBOXYLATE AND RHODIUM(II) CARBOXAMIDE CATALYZED CARBON-HYDROGEN INSERTION REACTIONS OF N,N-DISUBSTITUTED DIAZOACETOACETAMIDES [J].

DOYLE, MP ;

TAUNTON, J ;

PHO, HQ .

TETRAHEDRON LETTERS, 1989, 30 (40) :5397-5400

[9] ASYMMETRIC-SYNTHESIS OF LACTONES WITH HIGH ENANTIOSELECTIVITY BY INTRAMOLECULAR CARBON HYDROGEN INSERTION REACTIONS OF ALKYL DIAZOACETATES CATALYZED BY CHIRAL RHODIUM(II) CARBOXAMIDES [J].

DOYLE, MP ;

VANOEVEREN, A ;

WESTRUM, LJ ;

PROTOPOPOVA, MN ;

CLAYTON, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8982-8984

[10] CYCLOHEPTATRIENE SYNTHESES THROUGH RHODIUM(II) ACETATE-CATALYZED INTRAMOLECULAR ADDITION-REACTIONS OF N-BENZYLDIAZOACETAMIDES [J].

DOYLE, MP ;

SHANKLIN, MS ;

PHO, HQ .

TETRAHEDRON LETTERS, 1988, 29 (22) :2639-2642

← 1 2 3 4 →