HIGHLY STEREOCONTROLLED AND CONCISE ASYMMETRIC-SYNTHESIS OF THE BETA-LACTAM FRAMEWORK VIA A TCC METHOD

被引:8
作者
ASAO, N [1 ]
SHIMADA, T [1 ]
TSUKADA, N [1 ]
YAMAMOTO, Y [1 ]
机构
[1] TOHOKU UNIV,FAC SCI,DEPT CHEM,SENDAI,MIYAGI 98077,JAPAN
关键词
D O I
10.1016/S0040-4039(00)74424-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The conjugate addition of LSA 1 to t-butyl (4S)4-(trilyl)oxy-2-pentenoate 2d followed by aldol condensation with acetaldehyde produces a key intermediate 3 to beta-lactam derivatives as a single diastereoisomer in 77% yield.
引用
收藏
页码:8425 / 8428
页数:4
相关论文
共 22 条
[1]   ASYMMETRIC-SYNTHESIS OF THE BETA-LACTAM FRAMEWORK VIA A 3-COMPONENT COUPLING REACTION [J].
ASAO, N ;
TSUKADA, N ;
YAMAMOTO, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (21) :1660-1662
[2]   METAL-AMIDES IN ORGANIC-SYNTHESIS .7. STEREODIVERGENT SYNTHESIS OF THE ENOLATES OF A BETA-AMINO ESTER BY USING LITHIUM N-BENZYLTRIMETHYLSILYLAMIDE [J].
ASAO, N ;
UYEHARA, T ;
YAMAMOTO, Y .
TETRAHEDRON, 1990, 46 (13-14) :4563-4572
[3]  
BACKES J, 1991, METHODEN ORGANISCHEN, P31
[4]  
BROWN MJ, 1989, HETEROCYCLES, V29, P2225
[5]  
COPPER RDG, 1987, PURE APPL CHEM, V59, P485
[6]   ASYMMETRIC 1,4-ADDITIONS TO 5-ALKOXY-2(5H)-FURANONES ENANTIOSELECTIVE SYNTHESIS AND ABSOLUTE-CONFIGURATION DETERMINATION OF BETA-AMINO-GAMMA-BUTYROLACTONES AND AMINO DIOLS [J].
DELANGE, B ;
VANBOLHUIS, F ;
FERINGA, BL .
TETRAHEDRON, 1989, 45 (21) :6799-6818
[7]  
DONDONI A, 1993, SYNLETT, P256
[8]  
GEORG GI, 1992, ORGANIC CHEM BETA LA, P295
[9]  
GEORG GI, 1989, STUDIES NATURAL PROD, V4, P431
[10]  
Ghosez L., 1991, COMPREHENSIVE ORGANI, V5, P85