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.
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页码:425 / 435
页数:11
相关论文
共 49 条
[21]   ALDOL CONDENSATION OF DIMETHYLALUMINUM 4,4-DIMETHYLPENT-2-EN-2-OLATE - SOME NEW DIMETHYLALUMINUM KETOLATES [J].
JEFFERY, EA ;
MEISTERS, A ;
MOLE, T .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 74 (03) :373-384
[22]   TETRAKIS[IODO(TRI-NORMAL-BUTYLPHOSPHINE)-COPPER(I)] AND IODO-(2,2'-BIPYRIDINE)-(TRI-NORMAL-BUTYLPHOSPHINE)COPPER(I) [J].
KAUFFMAN, GB ;
TETER, LA .
INORGANIC SYNTHESES, 1963, 7 :9-12
[23]  
KUROZUMI S, 1976, TETRAHEDRON LETT, P4091
[24]  
MCKILLOP A, 1970, ACC CHEM RES, V3, P338
[25]  
MCKILLOP A, 17 P RA WELCH F C, P171
[26]  
MCMURRY JE, 1972, J AM CHEM SOC, V94, P7312
[27]   SYNTHESIS OF KETONES FROM DIHYDRO-1,3-OXAZINES VIA STEPWISE ALKYL OR ARYL INTRODUCTION [J].
MEYERS, AI ;
SMITH, EM .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (26) :4289-4293
[28]  
MORRIS RW, 1972, PROJECT REPORT U OTA
[29]   REGIOSPECIFIC ACYLATION, ALKYLATION, AND ALDOL CONDENSATION USING MAGNESIUM ENOLATES RESULTING FROM CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO ALPHA,BETA-UNSATURATED KETONES [J].
NAF, F ;
DECORZAN.R .
HELVETICA CHIMICA ACTA, 1974, 57 (05) :1317-1327
[30]   REGIOSPECIFIC INTRAMOLECULAR ALDOL CONDENSATION INDUCED BY CONJUGATE ADDITION OF LITHIUM DIMETHYLCUPRATE TO ZETA-OXO-ALPHA, BETA-ENONES [J].
NAF, F ;
DECORZANT, R ;
THOMMEN, W .
HELVETICA CHIMICA ACTA, 1975, 58 (06) :1808-1812