A DIRECT PREPARATION OF VINYLOGOUS ACYL ANION EQUIVALENTS

被引:25
作者
RAO, CJ [1 ]
KNOCHEL, P [1 ]
机构
[1] UNIV MICHIGAN,DEPT CHEM,WILLARD H DOW LABS,ANN ARBOR,MI 48109
关键词
D O I
10.1021/jo00015a004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Unmasked vinylogous acyl anion equivalents 2 were prepared by the insertion of zinc to various beta-halo, alpha,beta-unsaturated ketones and esters 1. The new reagents 2 react with various electrophiles in the presence of CuCN.2LiCl or catalytic amounts of Pd(0) complexes in excellent yields.
引用
收藏
页码:4593 / 4596
页数:4
相关论文
共 40 条
[1]   SYNTHESIS OF 4,5,6,7-TETRAHYDRO-1(3H)-ISOBENZOFURANONES BY REACTION OF N,N-DIMETHYL-2-LITHIO-1-CYCLOHEXENECARBOXAMIDE WITH ALDEHYDES AND KETONES [J].
BAKER, WR ;
COATES, RM .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (06) :1022-1024
[2]  
BAKUZIS P, 1978, TETRAHEDRON LETT, P2371
[3]  
CAINE D, 1978, TETRAHEDRON LETT, P5167
[4]   PREPARATIVE METHODS FOR BETA-ACYL VINYL ANION EQUIVALENTS FROM ENONES OR ALLYL SULFIDES [J].
COHEN, T ;
BENNETT, DA ;
MURA, AJ .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (14) :2506-2507
[5]   VERSATILE AND EXPEDIENT SYNTHESIS OF ALPHA,BETA-UNSATURATED KETONES - UTILIZATION OF BETA-EPOXY SULFONE FUNCTIONAL-GROUP AS ENONE PROGENITOR [J].
CONRAD, PC ;
FUCHS, PL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (01) :346-348
[6]  
DEBAL A, 1977, TETRAHEDRON LETT, P3187
[7]  
HASE TA, 1987, UMPOLUN SYNTHONS
[8]   GENERATION OF 3-CARBANION SPECIES FROM 3-PHENYLSULFINYL AND 3-PHENYLSULFONYL PROPIONIC ACIDS [J].
IWAI, K ;
KOSUGI, H ;
MIYAZAKI, A ;
UDA, H .
SYNTHETIC COMMUNICATIONS, 1976, 6 (05) :357-363
[9]  
KNOCHEL P, 1982, SYNTHESIS-STUTTGART, P1017
[10]   SYNTHESIS AND REACTIVITY TOWARD ACYL CHLORIDES AND ENONES OF THE NEW HIGHLY FUNCTIONALIZED COPPER REAGENTS RCU(CN)ZNI [J].
KNOCHEL, P ;
YEH, MCP ;
BERK, SC ;
TALBERT, J .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2390-2392