LITHIUM (ALPHA-METHYLBENZYL)ALLYLAMIDE - A DIFFERENTIALLY PROTECTED CHIRAL AMMONIA EQUIVALENT FOR THE ASYMMETRIC-SYNTHESIS OF BETA-AMINO ACIDS AND BETA-LACTAMS

被引:76
作者
DAVIES, SG
FENWICK, DR
机构
关键词
D O I
10.1039/c39950001109
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The addition products from the highly stereoselective conjugate additions of lithium (alpha S)-(alpha-methylbenzyl)allylamide to alpha,beta-unsaturated tert-butyl esters are efficiently deallylated with tris(triphenylphosphine)rhodium(I) chloride and converted, after transesterification to the methyl esters and cyclisation with methylmagnesium bromide, to the corresponding homochiral N-(alpha-methylbenzyl)-4-substituted-azetidin-2-ones.
引用
收藏
页码:1109 / 1110
页数:2
相关论文
共 28 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]   ASYMMETRIC-SYNTHESIS OF BETA-AMINO-ALPHA-HYDROXY ACIDS VIA DIASTEREOSELECTIVE HYDROXYLATION OF HOMOCHIRAL BETA-AMINO ENOLATES [J].
BUNNAGE, ME ;
CHERNEGA, AN ;
DAVIES, SG ;
GOODWIN, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (17) :2373-2384
[3]   ASYMMETRIC MICHAEL ADDITIONS OF HOMOCHIRAL MAGNESIUM AMIDES [J].
BUNNAGE, ME ;
DAVIES, SG ;
GOODWIN, CJ ;
WALTERS, IAS .
TETRAHEDRON-ASYMMETRY, 1994, 5 (01) :35-36
[4]   AN EXPEDITIOUS ASYMMETRIC-SYNTHESIS OF ALLOPHENYLNORSTATINE [J].
BUNNAGE, ME ;
DAVIES, SG ;
GOODWIN, CJ ;
ICHIHARA, O .
TETRAHEDRON, 1994, 50 (13) :3975-3986
[5]  
BUNNAGE ME, 1993, SYNLETT, P731
[6]  
BUNNAGE ME, 1994, TETRAHEDRON-ASYMMETR, V5, P203
[7]   ASYMMETRIC-SYNTHESIS OF THE TAXOL AND TAXOTERE C-13 SIDE-CHAINS [J].
BUNNAGE, ME ;
DAVIES, SG ;
GOODWIN, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (17) :2385-2391
[8]   ASYMMETRIC-SYNTHESIS OF HOMOCHIRAL SYN-3-PHENYLISOSERINE AND ANTI-3-PHENYLISOSERINE DERIVATIVES - A PRACTICAL STRATEGY FOR THE SYNTHESIS OF THE TAXOL C-13 SIDE-CHAIN [J].
BUNNAGE, ME ;
DAVIES, SG ;
GOODWIN, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (13) :1375-1376
[9]   ASYMMETRIC-SYNTHESIS OF THE N-TERMINAL COMPONENT OF MICROGININ - (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID, ITS (2R,3R)-EPIMER AND (3R)-3-AMINODECANOIC ACID [J].
BUNNAGE, ME ;
BURKE, AJ ;
DAVIES, SG ;
GOODWIN, CJ .
TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :165-176
[10]  
COLE DC, 1994, TETRAHEDRON, V50, P9515