ASYMMETRIC CATALYSIS .65. ENANTIOSELECTIVE ALKYLATION OF ALPHA-ISOPROPYL-3,4-DIMETHOXYBENZYLCYANIDE

被引:15
作者
BRUNNER, H
ZINTL, H
机构
来源
MONATSHEFTE FUR CHEMIE | 1991年 / 122卷 / 10期
关键词
MICHAEL REACTION; ALLYLATION; ENANTIOSELECTIVITY; PD-CATALYSIS;
D O I
10.1007/BF00815922
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The base-catalyzed Michael reaction and the palladium-catalyzed allylation were used to build up the quaternary asymmetric center of the Verapamil skeleton by enantioselective alkylation of alpha-isopropyl-3,4-dimethoxybenzylcyanide. Optical inductions up to 10.5% ee were achieved.
引用
收藏
页码:841 / 848
页数:8
相关论文
共 17 条
[1]  
BLASCHKE G, 1979, ARZNEIMITTEL-FORSCH, V29-2, P1640
[2]  
BRUNNER H, 1988, SYNTHESIS-STUTTGART, P645
[3]   ENANTIOSELECTIVE CATALYSIS .62. 1,2-BIS(DIMETHYLPHOSPHINO)ETHANE [J].
BRUNNER, H ;
ZIEGLER, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 397 (02) :C25-C27
[4]  
BRUNNER H, IN PRESS J ORGANOMET
[5]  
BRUNNER H, 1988, TOP STEREOCHEM, V18, P129
[6]   ASYMMETRIC INDUCTION IN THE MICHAEL REACTION BY MEANS OF CHIRAL PHASE-TRANSFER CATALYSTS DERIVED FROM CINCHONA AND EPHEDRA ALKALOIDS [J].
COLONNA, S ;
RE, A ;
WYNBERG, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (02) :547-552
[7]   CHIRAL MICHAEL ADDITION - METHYL VINYL KETONE ADDITION CATALYZED BY CINCHONA ALKALOID DERIVATIVES [J].
CONN, RSE ;
LOVELL, AV ;
KARADY, S ;
WEINSTOCK, LM .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (24) :4710-4711
[8]  
Coulson DR, 1971, INORG SYN, V13, P121, DOI DOI 10.1002/9780470132449.CH23
[9]   ASYMMETRICAL SYNTHESIS [J].
ENDERS, D ;
HOFFMANN, RW .
CHEMIE IN UNSERER ZEIT, 1985, 19 (06) :177-190
[10]   METAL PI-ALLYL CHEMISTRY .3. PREPARATION OF PI-ALLYLPALLADIUM COMPLEXES FROM PALLADIUM(II) SALTS [J].
HARTLEY, FR ;
JONES, SR .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 66 (03) :465-473