Nickel-catalyzed coupling reaction of sterically congested cis bromides and lithium alkenylborates

被引:37
作者
Kobayashi, Y [1 ]
Nakayama, Y [1 ]
Mizojiri, R [1 ]
机构
[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 226, Japan
关键词
D O I
10.1016/S0040-4020(97)10206-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lithium alkenyl berates of general structure 5 (RT = alkenyl) couple with cis bromides 1 at room temperature overnight in the presence of NiCl2(PPh3)(2) as a catalyst to furnish dienes of general structure 3 with retention of the olefin geometries present in both coupling partners. By using this reaction, cis,trans dienes 3 (R = TBDMS, TES, TBDPS; R-1 = n-C5H11, c-C6H11; R-2 = H; R-3 = n-C5H11, Ph) and cis,cis diene 3 (R = TBDMS; R-1 = R-2 = n-C5H11; R-3 = H) are synthesized in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1053 / 1062
页数:10
相关论文
共 20 条
[1]  
BJORKLING F, 1987, J ORG CHEM, V52, P292
[2]   Determination of the relative and absolute stereochemistry of fostriecin (CI-920) [J].
Boger, DL ;
Hikota, M ;
Lewis, BM .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1748-1753
[3]   ORGANOBORANES .30. CONVENIENT PROCEDURES FOR THE SYNTHESIS OF ALKYLBORONIC AND ALKENYLBORONIC ACIDS AND ESTERS [J].
BROWN, HC ;
BHAT, NG ;
SOMAYAJI, V .
ORGANOMETALLICS, 1983, 2 (10) :1311-1316
[4]   ORGANOBORANES .31. A SIMPLE PREPARATION OF BORONIC ESTERS FROM ORGANO-LITHIUM REAGENTS AND SELECTED TRIALKOXYBORANES [J].
BROWN, HC ;
COLE, TE .
ORGANOMETALLICS, 1983, 2 (10) :1316-1319
[5]   A highly efficient total synthesis of (+)-himbacine [J].
Chackalamannil, S ;
Davies, RJ ;
Asberom, T ;
Doller, D ;
Leone, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (40) :9812-9813
[6]   SYNTHESIS OF FUNCTIONALIZED 1-ALKENYLBORONATES VIA HYDROBORATION-DEALKYLATION OF ALKYNES WITH DIISOPINOCAMPHEYLBORANE [J].
KAMABUCHI, A ;
MORIYA, T ;
MIYAURA, N ;
SUZUKI, A .
SYNTHETIC COMMUNICATIONS, 1993, 23 (20) :2851-2859
[7]   A HIGHLY EFFICIENT KINETIC RESOLUTION OF GAMMA-TRIMETHYLSILYL AND BETA-TRIMETHYLSILYL SECONDARY ALLYLIC ALCOHOLS BY THE SHARPLESS ASYMMETRIC EPOXIDATION [J].
KITANO, Y ;
MATSUMOTO, T ;
SATO, F .
TETRAHEDRON, 1988, 44 (13) :4073-4086
[8]   STUDIES IN PROSTAGLANDINS .10. SYNTHESIS OF PROSTAGLANDIN MODELS AND PROSTAGLANDINS BY CONJUGATE ADDITION OF A FUNCTIONALIZED ORGANOCOPPER REAGENT [J].
KLUGE, AF ;
UNTCH, KG ;
FRIED, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (22) :7827-&
[9]   Nickel-catalyzed coupling reaction of lithium organoborates and aryl mesylates possessing an electron withdrawing group [J].
Kobayashi, Y ;
Mizojiri, R .
TETRAHEDRON LETTERS, 1996, 37 (47) :8531-8534
[10]   Nickel-catalyzed coupling reaction of 1,3-disubstituted secondary allylic carbonates and lithium aryl- and alkenylborates [J].
Kobayashi, Y ;
Mizojiri, R ;
Ikeda, E .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5391-5399