PREPARATION OF 2-ARYL-SUBSTITUTED AND 2-ALKENYL-SUBSTITUTED CARBAPENEMS UNDER MILD SUZUKI CROSS-COUPLING CONDITIONS

被引:37
作者
YASUDA, N
XAVIER, L
RIEGER, DL
LI, YL
DECAMP, AE
DOLLING, UH
机构
[1] Department of Process Research, Merck Research Laboratories, Rahway, NJ 07065
关键词
D O I
10.1016/S0040-4039(00)73663-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An extraordinarily mild procedure for the synthesis of 2-aryl- and 2-alkenyl-substituted carbapenems via palladium-catalyzed coupling of a vinyl triflate with aryl or vinyl boronic acids is described. A major advantage of this procedure is the use of nontoxic boronic acid intermediates in place of highly toxic organostannane compounds which are used in the corresponding Stille cross-coupling reactions.
引用
收藏
页码:3211 / 3214
页数:4
相关论文
共 22 条
[1]   PALLADIUM IN CEPHALOSPORIN CHEMISTRY - MILD TRIFLATE COUPLINGS IN THE ABSENCE OF PHOSPHINES AND HALIDE DONORS [J].
BAKER, SR ;
ROTH, GP ;
SAPINO, C .
SYNTHETIC COMMUNICATIONS, 1990, 20 (14) :2185-2189
[2]   HYDROBORATION .39. 1,3,2-BENZODIOXABOROLE (CATECHOLBORANE) AS A NEW HYDROBORATION REAGENT FOR ALKENES AND ALKYNES - GENERAL SYNTHESIS OF ALKANEBORONIC AND ALKENEBORONIC ACIDS AND ESTERS VIA HYDROBORATION - DIRECTIVE EFFECTS IN HYDROBORATION OF ALKENES AND ALKYNES WITH CATECHOLBORANE [J].
BROWN, HC ;
GUPTA, SK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (18) :5249-5255
[3]   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
[4]   PALLADIUM CATALYSIS IN CEPHALOSPORIN CHEMISTRY - GENERAL METHODOLOGY FOR THE SYNTHESIS OF CEPHEM SIDE-CHAINS [J].
FARINA, V ;
BAKER, SR ;
BENIGNI, DA ;
HAUCK, SI ;
SAPINO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5833-5847
[5]   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
[6]   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
[7]  
FLORENTIN D, 1976, B SOC CHIM FR II-CH, P1999
[8]   CONVENIENT SYNTHESIS OF VARIOUS TERHETEROCYCLIC COMPOUNDS BY PD(O)-CATALYZED COUPLING REACTIONS [J].
GRONOWITZ, S ;
PETERS, D .
HETEROCYCLES, 1990, 30 (01) :645-658
[9]   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
[10]  
KAHAN JS, 1979, J ANTIBIOT, V32, P1