Highly stereoselective ring-opening addition of terminal acetylenes to bicyclic olefins catalyzed by nickel complexes

被引:92
作者
Rayabarapu, DK [1 ]
Chiou, CF [1 ]
Cheng, CH [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan
关键词
D O I
10.1021/ol025731d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Treatment of 7-oxa- and 7-azabonzonorbornadienes with terminal acetylenes in the presence of Ni(dppe)Cl-2, ZnCl2, and Zn powder in toluene at 90 degreesC afforded the corresponding cis-2-alkynyl-1,2-dihydronaphthalene derivatives in moderate to excellent yields with remarkably high stereoselectivity.
引用
收藏
页码:1679 / 1682
页数:4
相关论文
共 48 条
[1]   A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes [J].
Anand, NK ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9687-9688
[2]   BASE-INDUCED BRIDGE CLEAVAGE OF 1,5-DIMETHYL-7-OXABICYCLO[2.2.1]HEPT-5-ENE SYSTEMS [J].
ARJONA, O ;
CONDO, S ;
PLUMET, J ;
VISO, A .
TETRAHEDRON LETTERS, 1995, 36 (34) :6157-6158
[3]   RING-OPENING REACTIONS OF CYCLIC ALLYLIC ETHERS BY ZIRCONOCENE COMPLEXES OF CYCLIC ALKYNES [J].
CUNY, GD ;
BUCHWALD, SL .
ORGANOMETALLICS, 1991, 10 (01) :363-365
[4]   PALLADIUM-CATALYZED STEREOSELECTIVE REDUCTIVE COUPLING REACTIONS OF ORGANIC HALIDES WITH 7-HETEROATOM NORBORNADIENES [J].
DUAN, JP ;
CHENG, CH .
TETRAHEDRON LETTERS, 1993, 34 (25) :4019-4022
[5]   Nickel-catalyzed highly stereoselective ring opening of 7-oxa- and azanorbornenes with organic halides [J].
Feng, CC ;
Nandi, M ;
Sambaiah, T ;
Cheng, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3538-3543
[6]  
Fugami K, 1998, SYNLETT, P477
[7]   PHOSPHIDES AND ARSENIDES AS METAL HALOGEN EXCHANGE REAGENTS .2. REACTIONS WITH AROMATIC DIHALIDES [J].
GILLESPIE, DG ;
WALKER, BJ ;
STEVENS, D ;
MCAULIFFE, CA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08) :1697-1703
[8]   Nickel-promoted first ene-diyne cycloaddition reaction on C60:: Synthesis and photochemistry of the fullerene derivatives [J].
Hsiao, TY ;
Santhosh, KC ;
Liou, KF ;
Cheng, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (47) :12232-12236
[9]   Nickel-catalyzed cocyclotrimerization of oxa- and azabenzonorbornadienes with alkynes: reaction with multiple synthetic applications [J].
Huang, DJ ;
Sambaiah, T ;
Cheng, CH .
NEW JOURNAL OF CHEMISTRY, 1998, 22 (11) :1147-1149
[10]  
Huang DJ, 2000, CHEM-EUR J, V6, P3706, DOI 10.1002/1521-3765(20001016)6:20<3706::AID-CHEM3706>3.0.CO