CONJUGATE ADDITION OF ORGANOCUPRATES TO GAMMA-METHYL-DELTA-OXY-ALPHA,BETA-ENONES - INFLUENCE OF THE ALKOXY SUBSTITUENT ON THE DIASTEREOSELECTION

被引:9
作者
COURTEMANCHE, G
ALEXAKIS, A
VAISSERMANN, J
NORMANT, JF
机构
[1] UNIV PARIS 06,CHIM ORGANOELEMENTS LAB,4 PL JUSSIEU,F-75252 PARIS 05,FRANCE
[2] UNIV PARIS 06,CHIM MET TRANSIT LAB,F-75252 PARIS 05,FRANCE
关键词
D O I
10.1016/0022-328X(92)83121-W
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The stereochemistry of the conjugate addition of cuprates to the title compounds is mainly governed by the gamma-methyl group, but the alkoxy substituent also plays a role.
引用
收藏
页码:281 / 305
页数:25
相关论文
共 73 条
[1]   THE CONJUGATE ADDITION OF A SILYL GROUP TO ENONES AND ITS REMOVAL WITH COPPER(II) BROMIDE - A PROTECTING GROUP FOR THE ALPHA-BETA-UNSATURATION OF ALPHA-BETA-UNSATURATED KETONES [J].
AGER, DJ ;
FLEMING, I ;
PATEL, SK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (09) :2520-2526
[2]  
ALEXAKIS A, 1978, TETRAHEDRON LETT, P4205
[3]   ORGANOCOPPER CONJUGATE ADDITION-REACTION IN THE PRESENCE OF TRIMETHYLCHLOROSILANE [J].
ALEXAKIS, A ;
BERLAN, J ;
BESACE, Y .
TETRAHEDRON LETTERS, 1986, 27 (09) :1047-1050
[4]   STEREOCHEMICAL EFFECTS OF TRIMETHYLSILYL CHLORIDE (TMSCL) ON THE CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS [J].
ALEXAKIS, A ;
SEDRANI, R ;
MANGENEY, P .
TETRAHEDRON LETTERS, 1990, 31 (03) :345-348
[5]   SYNTHESIS OF 25-HYDROXY-VITAMIN-D3 AND 1-ALPHA,25-DIHYDROXYVITAMIN-D3 FROM VITAMIN-D2 (CALCIFEROL) [J].
ANDREWS, DR ;
BARTON, DHR ;
HESSE, RH ;
PECHET, MM .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4819-4828
[6]   DIASTEREOSELECTIVE ADDITION OF THE 2-PHENYLSULFONYL-SUBSTITUTED ALLYLIC BROMIDES TO ALDEHYDES IN THE PRESENCE OF ZINC OR CHROMIUM (II) CHLORIDE [J].
AUVRAY, P ;
KNOCHEL, P ;
NORMANT, JF .
TETRAHEDRON LETTERS, 1986, 27 (42) :5091-5094
[7]  
AUVRAY P, 1990, B SOC CHIM FR, P813
[8]  
AUVRAY P, 1988, THESIS PARIS
[9]   ORGANOCOPPER-IODOSILANE COMBINATIONS IN CONJUGATE ADDITIONS [J].
BERGDAHL, M ;
LINDSTEDT, EL ;
NILSSON, M ;
OLSSON, T .
TETRAHEDRON, 1989, 45 (02) :535-543
[10]   CHLOROTRIMETHYLSILANE-ACTIVATED AND IODOTRIMETHYLSILANE-ACTIVATED ADDITIONS OF ORGANOCOPPER COMPOUNDS TO ENONES AND ENOATES [J].
BERGDAHL, M ;
LINDSTEDT, EL ;
NILSSON, M ;
OLSSON, T .
TETRAHEDRON, 1988, 44 (07) :2055-2062