ORGANOMETALLIC REAGENTS IN ORGANIC-SYNTHESIS .5. ORGANOCUPRATE CONJUGATE ADDITION - ALDOL CONDENSATION SYNTHETIC PROCEDURE FOR SEQUENTIAL FORMATION OF 2 CARBON-CARBON BONDS

被引:56
作者
HENG, KK [1 ]
SMITH, RAJ [1 ]
机构
[1] UNIV OTAGO,DEPT CHEM,DUNEDIN,NEW ZEALAND
关键词
D O I
10.1016/0040-4020(79)80083-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enolates produced from the conjugate addition reaction of lithium dialkylcuprates with α,β- unsaturated ketones react with aldehydes in the presence of zinc chloride to give overall β-alkyl α-hydroxyalkyl addition to the original alkene. Reaction of these enolates with carbon dioxide and ethyl formate is also reported. © 1979.
引用
收藏
页码:425 / 435
页数:11
相关论文
共 49 条
[1]   REGIOSPECIFIC ALKYLATION OF ORGANOCOPPER ENOLATES [J].
BOECKMAN, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (26) :4450-4452
[2]   CONJUGATE ADDITION-ANNELATION - HIGHLY REGIOSPECIFIC AND STEREOSPECIFIC SYNTHESIS OF POLYCYCLIC KETONES [J].
BOECKMAN, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (20) :6867-6869
[3]   CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT [J].
BORCH, RF ;
BERNSTEIN, MD ;
DURST, HD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :2897-+
[4]  
BRINKLEY ES, 1975, J ORG CHEM, V40, P2156
[5]   CONJUGATE-ADDITION ALKYLATION OF ALPHA,BETA-UNSATURATED KETONES [J].
COATES, RM ;
SANDEFUR, LO .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (02) :275-277
[6]   SITE-SELECTIVE GEMINAL ALKYLATION OF KETONES - REDUCTION-ALKYLATION OF BURYLTHIOMETHYLENE DERIVATIVES [J].
COATES, RM ;
SOWERBY, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (04) :1027-&
[7]  
CONIA JM, 1975, B SOC CHIM FR, P2722
[8]  
FELKIN H, UNPUBLISHED
[9]   THE ANALYSIS OF ORGANOLITHIUM COMPOUNDS [J].
GILMAN, H ;
CARTLEDGE, FK .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1964, 2 (06) :447-454
[10]   ACTIVATION OF MANGANESE DIOXIDE BY AZEOTROPIC REMOVAL OF WATER [J].
GOLDMAN, IM .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (06) :1979-&