DIASTEREOSELECTIVE STEREODIVERGENT ADDITION OF E-CROTYLSILANES AND Z-CROTYLSILANES TO 2-CYCLOPENTENONE DERIVATIVES WITH CHIRAL AUXILIARIES AT 2-POSITION

被引:22
作者
PAN, LR [1 ]
TOKOROYAMA, T [1 ]
机构
[1] OSAKA CITY UNIV,FAC SCI,SUMIYOSHI KU,OSAKA 558,JAPAN
关键词
EXTRACYCLIC STEREOCONTROL; SAKURAI REACTION; STEREODIVERGENT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS;
D O I
10.1016/S0040-4039(00)91649-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Simple and diastereo-face selectivities in the addition reaction of E- and Z-crotylsilanes to chiral 2-p-tolyl-sulfinyl- and 2-menthoxy-2-cyclopentenones have been investigated to define the conditions for the stereodivergent enantioselective synthesis of the cyclopentenone derivatives with extracyclic stereogenic centers.
引用
收藏
页码:1469 / 1472
页数:4
相关论文
共 12 条
[1]   STEREOSELECTIVE CYCLIZATION OF (E)-5,6-DIMETHYL-8-TRIMETHYLSILYL-6-OCTENALS AND (Z)-5,6-DIMETHYL-8-TRIMETHYLSILYL-6-OCTENALS [J].
ASAO, K ;
IIO, H ;
TOKOROYAMA, T .
TETRAHEDRON LETTERS, 1989, 30 (46) :6397-6400
[2]  
BUSCHMANN H, 1988, SYNTHESIS-STUTTGART, P827
[3]   PREPARATION OF AN OPTICALLY-ACTIVE PROSTAGLANDIN INTERMEDIATE VIA ASYMMETRIC INDUCTION [J].
COREY, EJ ;
ENSLEY, HE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (23) :6908-6909
[4]   STEREOCHEMICAL AND SPECTROSCOPIC STUDIES ON THE REACTION OF ALLYLSTANNANES WITH ALDEHYDES [J].
DENMARK, SE ;
WEBER, EJ ;
WILSON, TM ;
WILLSON, TM .
TETRAHEDRON, 1989, 45 (04) :1053-1065
[5]  
HULCE M, 1990, ORG SYNTH, V7, P495
[6]   SYNTHETIC STUDIES ON TERPENOID COMPOUNDS .34. EXTRACYCLIC STEREOCONTROL IN ADDITION-REACTION OF CROTYLSILANES WITH 2-SUBSTITUTED 2-CYCLOPENTENONES - STEREODIVERGENT SYNTHESIS OF (+)-NEONEPETALACTONE AND (+)-ISONEONEPETALACTONE [J].
PAN, LR ;
TOKOROYAMA, T .
CHEMISTRY LETTERS, 1990, (11) :1999-2002
[7]   ASYMMETRIC SYNTHESES OF DE-ABC-CHOLESTAN-14-ONE AND DE-AB-CHOLEST-8-EN-9-ONE BY AN EXTRACYCLIC METHODOLOGY [J].
PAN, LR ;
TOKOROYAMA, T .
TETRAHEDRON LETTERS, 1992, 33 (11) :1473-1474
[8]   ASYMMETRIC-SYNTHESIS OF CARBON CARBON BONDS USING SULFINYL CYCLOALKENONES, ALKENOLIDES, AND PYRONES [J].
POSNER, GH .
ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (02) :72-78
[9]   ASYMMETRIC-SYNTHESIS USING ENANTIOMERICALLY PURE 2-(PARA-ANISYLSULFINYL)-2-CYCLOALKENONES [J].
POSNER, GH ;
FRYE, LL ;
HULCE, M .
TETRAHEDRON, 1984, 40 (08) :1401-1407
[10]  
POSNER GH, 1983, ASYMMETRIC SYNTHESIS, V2, P235