NICKEL-PROMOTED INTRAMOLECULAR CYCLIZATION OF VINYL BROMIDES WITH ALKENES AND ALKYNES

被引:8
作者
LLEBARIA, A
CAMPS, F
MORETO, J
机构
[1] Department of Biological Organic Chemistry, C.I.D. (C.S.I.C) Jordi Girona 18-26
关键词
D O I
10.1016/S0040-4039(00)92536-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of vinyl bromides bearing distal olefin or acetylene functionalities with tetracarbonylnickel in the presence of alcohols and triethylamine results in the formation of exo-methylene cyclic esters in a regioselective process. High influence of the bulkiness of the alcohol is found.
引用
收藏
页码:3683 / 3686
页数:4
相关论文
共 19 条
[11]   A METHOD FOR 1,4 ADDITION OF ACYL GROUPS TO CONJUGATED ENONES [J].
COREY, EJ ;
HEGEDUS, LS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (17) :4926-&
[12]   THE SYNTHESIS OF BRIDGED-RING CARBOCYCLES AND HETEROCYCLES VIA PALLADIUM CATALYZED REGIOSPECIFIC CYCLIZATION REACTIONS [J].
GRIGG, R ;
SANTHAKUMAR, V ;
SRIDHARAN, V ;
STEVENSON, P ;
TEASDALE, A ;
THORNTONPETT, M ;
WORAKUN, T .
TETRAHEDRON, 1991, 47 (46) :9703-9720
[13]  
Mulzer J., 1991, ORGANIC SYNTHESIS HI
[14]   PALLADIUM(0) CATALYZED AND NICKEL(0) CATALYZED METALLO-ENE-TYPE CYCLIZATIONS - STEREODIRECTING RESIDENT CHIRALITY [J].
OPPOLZER, W ;
KELLER, TH ;
KUO, DL ;
PACHINGER, W .
TETRAHEDRON LETTERS, 1990, 31 (09) :1265-1268
[15]   TRANSITION-METAL-MEDIATED CYCLO-ADDITION REACTIONS OF ALKYNES IN ORGANIC-SYNTHESIS [J].
SCHORE, NE .
CHEMICAL REVIEWS, 1988, 88 (07) :1081-1119
[16]   INTRAMOLECULAR CARBONYLATION OF VINYL HALIDES TO FORM METHYLENE LACTONES [J].
SEMMELHACK, MF ;
BRICKNER, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (08) :1723-1726
[17]   METAL PROMOTED .9. - CONTROLLED AND CATALYTIC ACYLPALLADATION - A NOVEL ROUTE TO CYCLOPENTENONE AND CYCLOHEXENONE DERIVATIVES [J].
TOUR, JM ;
NEGISHI, EI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (26) :8289-8291
[18]   [3+2] CYCLOADDITION APPROACHES TO 5-MEMBERED RINGS VIA TRIMETHYLENEMETHANE AND ITS EQUIVALENTS [J].
TROST, BM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (01) :1-20
[19]   METAL-PROMOTED CYCLIZATION .25. PALLADIUM-CATALYZED CASCADE CARBOMETALATION OF ALKYNES AND ALKENES AS AN EFFICIENT ROUTE TO CYCLIC AND POLYCYCLIC STRUCTURES [J].
ZHANG, Y ;
NEGISHI, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3454-3456