ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION TO WINTERSTEIN ACID, R-3-DIMETHYLAMINO-3-PHENYL PROPIONIC-ACID, BY THE ASYMMETRIC-SYNTHESIS OF HOMOCHIRAL (S)-(+)-ETHYL 3-DIMETHYLAMINO-3-PHENYL PROPIONATE

被引:20
作者
DAVIES, SG
DUPONT, J
EASTON, RJC
机构
[1] The Dyson Perrins Laboratory, Oxford, OX1 3QY, South Park Road
关键词
D O I
10.1016/S0957-4166(00)86312-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The asymmetric synthesis of homochiral (S)-(+)-ethyl 3-dimethylamino-3-phenyl propionate, via stereoselective Michael addition of lithium dimethylamide to (S)-Z-[(η5-C5H5)-Fe(CO)(PPh3)COCHCHPh] and oxidative decomplexation, establishes the absolute configuration of Winterstein's acid, 3-dimethylamino-3-phenyl propionic acid, derived from Taxine B, as R. © 1990.
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页码:279 / 280
页数:2
相关论文
共 7 条
[1]   SYNTHESIS AND CHARACTERIZATION OF E-ALPHA,BETA-UNSATURATED AND Z-ALPHA,BETA-UNSATURATED ACYL COMPLEXES [(ETA-5-C5H5)FE(CO)(PPH3)(COCH=CHR)](R=H,ME,ET,NORMAL-BU,TERT-BU,PH,VINYL,2-FURYL) [J].
DAVIES, SG ;
EASTON, RJC ;
WALKER, JC ;
WARNER, P .
TETRAHEDRON, 1986, 42 (01) :175-188
[2]   THE ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS - STEREOCONTROLLED ASYMMETRIC TANDEM MICHAEL ADDITIONS AND SUBSEQUENT ALKYLATIONS OF E-[(ETA-5-C5H5)FE(CO)(PPH3)COCH=CHME] - X-RAY CRYSTAL-STRUCTURE OF (RS)-E-[(ETA-5-C5H5)FE(CO)(PPH3)COCH - CHME] [J].
DAVIES, SG ;
DORDORHEDGECOCK, IM ;
SUTTON, KH ;
WALKER, JC ;
JONES, RH ;
PROUT, K .
TETRAHEDRON, 1986, 42 (18) :5123-5137
[3]  
GRAF E, 1958, LIEBIGS ANN CHEM, V613, P111
[4]  
GRAF E, 1986, LIEBIGS ANN CHEM, V7, P1147
[5]   TRANSFORMATIONS OF CHIRAL IRON COMPLEXES USED IN ORGANIC-SYNTHESIS - REACTIONS OF ETA-5-CPFE(PPH3)(CO)COCH3 AND RELATED SPECIES LEADING TO A MILD, STEREOSPECIFIC SYNTHESIS OF BETA-LACTAMS [J].
LIEBESKIND, LS ;
WELKER, ME ;
FENGL, RW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6328-6343
[6]  
LUCAS H, 1856, ARCH PHARM, V95, P145
[7]   A BRIEF SURVEY OF TAXUS ALKALOIDS AND OTHER TAXANE DERIVATIVES [J].
MILLER, RW .
JOURNAL OF NATURAL PRODUCTS, 1980, 43 (04) :425-437