A HIGHLY EFFICIENT METHOD FOR THE PREPARATION OF 2-ARYL SUBSTITUTED CARBAPENEMS EXPLOITING A PD(0) MEDIATED CROSS-COUPLING REACTION

被引：41

作者：

RANO, TA

GREENLEE, ML

DININNO, FP

机构：

[1] Merck Sharp and Dohme Research Laboratories Rahway

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 20期

关键词：

D O I：

10.1016/0040-4039(90)80165-I

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A remarkably mild procedure for the synthesis of 2-aryl substituted carbapenems via a palladium catalyzed coupling reaction of a vinyl triflate with aryl stannanes is described. Employing Pd2(DBA)3.CHCl3 as the catalyst and tris(2,4,6-trimethoxyphenyl)phosphine as the ligand provides generous yields of the desired β-lactams. Reaction times are brief while reaction temperatures never exceed ambient. © 1990.

引用

收藏

页码：2853 / 2856

页数：4

相关论文

共 25 条

[1] CHELATE-ASSISTED, PD-CATALYZED EFFICIENT CARBONYLATION OF ARYL CHLORIDES [J].

BENDAVID, Y ;

PORTNOY, M ;

MILSTEIN, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8742-8744

[2] FORMYLATION OF ARYL CHLORIDES CATALYZED BY A PALLADIUM COMPLEX [J].

BENDAVID, Y ;

PORTNOY, M ;

MILSTEIN, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) :1816-1817

[3] TOTAL SYNTHESIS OF THIENAMYCIN ANALOGS .2. SYNTHESIS OF 2-ALKYL AND 2-ARYL THIENAMYCIN NUCLEI [J].

CAMA, L ;

CHRISTENSEN, BG .

TETRAHEDRON LETTERS, 1980, 21 (21) :2013-2016

[4] TOTAL SYNTHESIS OF THIENAMYCIN ANALOGS .3. SYNTHESES OF 2-ARYL AND 2-HETEROARYL ANALOGS OF THIENAMYCIN [J].

CAMA, LD ;

WILDONGER, KJ ;

GUTHIKONDA, R ;

RATCLIFFE, RW ;

CHRISTENSEN, BG .

TETRAHEDRON, 1983, 39 (15) :2531-2549

[5] PALLADIUM-CATALYZED CHEMISTRY OF BETA-LACTAM VINYL TRIFLATES - COUPLING WITH ORGANOSTANNANES AND ALKOXYCARBONYLATION [J].

COOK, GK ;

HORNBACK, WJ ;

JORDAN, CL ;

MCDONALD, JH ;

MUNROE, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (24) :5828-5830

[6] PALLADIUM-CATALYZED COUPLING BETWEEN CEPHALOSPORIN DERIVATIVES AND UNSATURATED STANNANES - A NEW LIGAND FOR PALLADIUM CHEMISTRY [J].

FARINA, V ;

BAKER, SR ;

BENIGNI, DA ;

SAPINO, C .

TETRAHEDRON LETTERS, 1988, 29 (45) :5739-5742

[7] PALLADIUM CATALYSIS IN CEPHALOSPORIN CHEMISTRY - A VERSATILE NEW APPROACH TO 3-SUBSTITUTED CEPHEMS [J].

FARINA, V ;

BAKER, SR ;

SAPINO, C .

TETRAHEDRON LETTERS, 1988, 29 (47) :6043-6046

[8] STRUCTURE-ACTIVITY-RELATIONSHIPS IN THE 2-ARYLCARBAPENEM SERIES - SYNTHESIS OF 1-METHYL-2-ARYLCARBAPENEMS [J].

GUTHIKONDA, RN ;

CAMA, LD ;

QUESADA, M ;

WOODS, MF ;

SALZMANN, TN ;

CHRISTENSEN, BG .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (05) :871-880

[9] MODIFICATION OF NATURAL-PRODUCTS TO IMPROVE THEIR BIOLOGICAL PROPERTIES [J].

GUTHIKONDA, RN ;

CAMA, LD ;

QUESADA, M ;

WOODS, MF ;

SALZMANN, TN ;

CHRISTENSEN, BG .

PURE AND APPLIED CHEMISTRY, 1987, 59 (03) :455-458

[10]

KAHAN JS, 1979, J ANTIBIOT, V32, P1