Preparation and reactions of acylzinc species

被引:7
作者
Chemla, F
Normant, JF
机构
[1] Lab. de Chim. des Organo-Elements, URA 473 CNRS, Univ. Pierre et Marie Curie, 75252 Paris Cedex 05, 4, Place Jussieu
关键词
D O I
10.1016/S0040-4020(97)10179-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reduction of acyl chlorides by zerovalent zinc dust is described. The reaction gives enol esters of (Z) configuration in high yields. The initial product is presumed to be an acyl zinc species, which gives the enol ester in a stereospecific manner by a 1,2-hydrogen shift on the carbene intermediate. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:17265 / 17274
页数:10
相关论文
共 39 条
[1]   REARRANGEMENT PRODUCTS OF A THERMALLY GENERATED OXYCARBENE [J].
AGOSTA, WC ;
FOSTER, AM .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (09) :433-&
[2]  
[Anonymous], CHEM ACYL HALIDES
[3]   ZINC-PROMOTED SELECTIVE CLEAVAGE OF ETHERS IN PRESENCE OF ACYL CHLORIDE [J].
BHAR, S ;
RANU, BC .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) :745-747
[4]  
BRUNEAU C, 1997, J CHEM SOC CHEM COMM, P507
[5]  
CHEMLA F, 1997, UNPUB SYNTH COMMUN
[6]   PREPARATION OF POLYFUNCTIONAL KETONES BY A COBALT(II) MEDIATED CARBONYLATION OF ORGANOZINC REAGENTS [J].
DEVASAGAYARAJ, A ;
KNOCHEL, P .
TETRAHEDRON LETTERS, 1995, 36 (46) :8411-8414
[7]   GENERAL-SYNTHESIS OF (Z)-ALK-1-EN-1-YL ESTERS VIA RUTHENIUM-CATALYZED ANTI-MARKOVNIKOV TRANS-ADDITION OF CARBOXYLIC-ACIDS TO TERMINAL ALKYNES [J].
DOUCET, H ;
MARTINVACA, B ;
BRUNEAU, C ;
DIXNEUF, PH .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7247-7255
[8]  
Fischer FG, 1933, LIEBIGS ANN CHEM, V500, P253
[9]   STEREOSPECIFIC SYNTHESIS OF HETEROATOM-SUBSTITUTED OLEFINS FROM ALPHA,BETA-EPOXYSILANES - PREPARATION OF VINYL BROMIDES, ENOL ACETATES, ENOL ETHERS, AND ENAMIDES [J].
HUDRLIK, PF ;
HUDRLIK, AM ;
RONA, RJ ;
MISRA, RN ;
WITHERS, GP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (06) :1993-1996
[10]   Carbonylative coupling of organozinc reagents in the presence and absence of aryl iodides: Synthesis of unsymmetrical and symmetrical ketones [J].
Jackson, RFW ;
Turner, D ;
Block, MH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (06) :865-870