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
[11]   HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF LEUKOTRIENE-B4, 20-HYDROXYLEUKOTRIENE-B4, LEUKOTRIENE-B3, AND THEIR ANALOGS [J].
KOBAYASHI, Y ;
SHIMAZAKI, T ;
TAGUCHI, H ;
SATO, F .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) :5324-5335
[12]   NEW STEREOSPECIFIC SYNTHESES OF PHEROMONE BOMBYKOL AND ITS 3 GEOMETRICAL-ISOMERS [J].
MIYAURA, N ;
SUGINOME, H ;
SUZUKI, A .
TETRAHEDRON, 1983, 39 (20) :3271-3277
[13]   NOVEL AND CONVENIENT METHOD FOR THE STEROSPECIFIC AND REGIOSPECIFIC SYNTHESIS OF CONJUGATED ALKADIENES AND ALKENYNES VIA THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 1-ALKENYLBORANES WITH BROMOALKENES AND BROMOALKYNES [J].
MIYAURA, N ;
YAMADA, K ;
SUGINOME, H ;
SUZUKI, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (04) :972-980
[14]   NICKEL-CATALYZED OR PALLADIUM-CATALYZED CROSS COUPLING .31. PALLADIUM-CATALYZED OR NICKEL-CATALYZED REACTIONS OF ALKENYLMETALS WITH UNSATURATED ORGANIC HALIDES AS A SELECTIVE ROUTE TO ARYLATED ALKENES AND CONJUGATED DIENES - SCOPE, LIMITATIONS, AND MECHANISM [J].
NEGISHI, E ;
TAKAHASHI, T ;
BABA, S ;
VANHORN, DE ;
OKUKADO, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (08) :2393-2401
[15]   A HIGHLY EFFICIENT SYNTHESIS OF GAMMA-HALO ALLYLIC ALCOHOLS AND PROPARGYLIC ALCOHOLS WITH HIGH OPTICAL PURITY - PRACTICAL METHOD FOR SYNTHESIS OF THE PROSTAGLANDIN OMEGA-CHAIN [J].
OKAMOTO, S ;
SHIMAZAKI, T ;
KOBAYASHI, Y ;
SATO, F .
TETRAHEDRON LETTERS, 1987, 28 (18) :2033-2036
[16]  
SATO F, 1992, SYNLETT, P849
[17]   MILD AND STEREOSELECTIVE HYDROBORATIONS OF FUNCTIONALIZED ALKYNES AND ALKENES USING PINACOLBORANE [J].
TUCKER, CE ;
DAVIDSON, J ;
KNOCHEL, P .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3482-3485
[18]   DRAMATIC RATE ENHANCEMENT OF SUZUKI DIENE SYNTHESIS - ITS APPLICATION TO PALYTOXIN SYNTHESIS [J].
UENISHI, J ;
BEAU, JM ;
ARMSTRONG, RW ;
KISHI, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) :4756-4758
[19]   TETRAHEDRAL NICKEL(II) COMPLEXES AND THE FACTORS DETERMING THEIR FORMATION .1. BISTRIPHENYLPHOSPHINE NICKEL(II) COMPOUNDS [J].
VENANZI, LM .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (FEB) :719-724
[20]  
TOTAL SYNTHESIS NATU