PALLADIUM-CATALYZED REACTION OF ARYL-SUBSTITUTED ALLYLIC ALCOHOLS WITH ZINC ENOLATES OF BETA-DICARBONYL COMPOUNDS IN THE PRESENCE OF TITANIUM(IV) ISOPROPOXIDE

被引:42
作者
ITOH, K [1 ]
HAMAGUCHI, N [1 ]
MIURA, M [1 ]
NOMURA, M [1 ]
机构
[1] OSAKA UNIV,FAC ENGN,DEPT APPL CHEM,SUITA,OSAKA 565,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 21期
关键词
D O I
10.1039/p19920002833
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of aryl-substituted allylic alcohols la-c with Zn(acac)2 using a catalytic amount of PdCl2(PPh3)2 proceeds efficiently in the presence of lithium chloride and titanium(IV) isopropoxide to give the corresponding acetonylated products 3-5. Similarly, benzoylmethylation and ethoxycarbonylmethylation of la and lb can also be attained by using zinc enolates generated in situ from reactions of zinc chloride with dibenzoylmethane 8b and ethyl benzoylacetate 8c.
引用
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页码:2833 / 2835
页数:3
相关论文
共 25 条
[1]  
ATKINS KE, 1970, TETRAHEDRON LETT, P3821
[2]   ALKYLATION OF ACTIVE METHYLENE-COMPOUNDS BY ALLYLIC ALCOHOLS USING TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0) CATALYSTS [J].
BERGBREITER, DE ;
WEATHERFORD, DA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (13) :883-884
[3]   STEREOSELECTIVE CONVERSION OF KETO GROUPS INTO METHYL VINYL QUATERNARY CARBON CENTERS [J].
BUCKWALTER, BL ;
BURFITT, IR ;
FELKIN, H ;
JOLYGOUDKET, M ;
NAEMURA, K ;
SALOMON, MF ;
WENKERT, E ;
WOVKULICH, PM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (20) :6445-6450
[4]   1,7-DIMETHYLCHRYSENE - PHOTOCYCLIZATION OF 1,6-DIARYLHEXA-1,3,5-TRIENES [J].
CARRUTHERS, W ;
EVANS, N ;
POORANAM.R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (01) :44-47
[5]   ASYMMETRIC-SYNTHESIS IN THE NICKEL-COMPLEX-CATALYZED FORMATION OF OLEFINS FROM ALLYL ALCOHOLS AND GRIGNARD-REAGENTS [J].
CHEREST, M ;
FELKIN, H ;
UMPLEBY, JD ;
DAVIES, SG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (14) :681-682
[6]   INFLUENCE OF COPPER ON SUBSTITUTION OF STABLE ENOLATES BY A VARIETY OF ALLYLIC HALIDES [J].
CUVIGNY, T ;
JULIA, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 331 (01) :121-137
[7]   The d- and 1-alpha-phenylallyl alcohols and some of their reactions [J].
Duveen, DI ;
Kenyon, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1939, :1697-1701
[8]   ACTIVATION OF GRIGNARD-REAGENTS BY TRANSITION-METAL COMPOUNDS [J].
FELKIN, H ;
SWIERCZEWSKI, G .
TETRAHEDRON, 1975, 31 (22) :2735-2748
[9]   ALKYLATION OF ALLYLIC DERIVATIVES .10. RELATIVE RATES OF REACTIONS OF ALLYLIC CARBOXYLATES WITH LITHIUM DIMETHYLCUPRATE [J].
GOERING, HL ;
KANTNER, SS ;
SEITZ, EP .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5495-5499
[10]  
HATCH LF, 1954, J AM CHEM SOC, V76, P2706