Transfer of alk-1-enyl group from boron to aluminium: a novel way to prepare (E)-alk-1-enyldiisobutylalanes

被引：10

作者：

Hoshi, M ^{[1
]}

Shirakawa, K ^{[1
]}

机构：

[1] Kitami Inst Technol, Dept Appl & Environm Chem, Kitami, Hokkaido 0908507, Japan

来源：

CHEMICAL COMMUNICATIONS | 2002年 / 18期

关键词：

D O I：

10.1039/b206541j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of (E)-alk-1-enyldicyclohexylboranes 1 with diisobutylaluminium hydride (DIBAL-H) in the presence of hex-1-ene at room temperature results in transfer of the alk-1-enyl group from boron to aluminium to give (E)-alk-1-enyldiisobutylalanes 2 with retention of configuration at the double bond.

引用

页码：2146 / 2147

页数：2

共 11 条

[1] Eisch JJ., 1995, COMPREHENSIVE ORGANO, V11, P277
[2] Transfer of alk-1-enyl group from boron to boron:: preparation of B-[(E)-alk-1-enyl]-9-borabicyclo[3.3.1]nonane
Hoshi, M
Shirakawa, K
Arase, A
[J]. CHEMICAL COMMUNICATIONS, 1998, (11) : 1225 - 1226
[3] ORGANOBORANES .13. MERCURATION OF VINYLBORANES - CONVENIENT STEREOSPECIFIC PROCEDURE FOR CONVERSION OF ACETYLENES INTO VINYLMERCURY SALTS VIA HYDROBORATION-MERCURATION
LAROCK, RC
BROWN, HC
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1972, 36 (01) : 1 - &
[4] REACTION OF 2-ALKENYL-1,3,2-BENZODIOXABOROLES WITH MERCURIC ACETATE - CONVENIENT STEREOSPECIFIC PROCEDURE FOR CONVERSION OF ALKYNES INTO ALKENYLMERCURIC SALTS
LAROCK, RC
GUPTA, SK
BROWN, HC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (12) : 4371 - &
[5] Matteson D. S., 1995, Stereodirected Synthesis with Organoboranes
[6] SELECTIVE CARBON-CARBON BOND FORMATION VIA TRANSITION-METAL CATALYSIS .30. A SELECTIVE AND CONVENIENT SYNTHESIS OF BETA,BETA-DIALKYL-SUBSTITUTED ALKENYLBORANES AND ALKENYLZIRCONIUMS VIA CARBOALUMINATION OF ALKYNES
NEGISHI, E
BOARDMAN, LD
[J]. TETRAHEDRON LETTERS, 1982, 23 (33) : 3327 - 3330
[7] PELTER A, 1979, COMPREHENSIVE ORGANI, V3, P791
[8] Pelter A., 1988, BORANE REAGENTS
[9] A NOVEL METHOD FOR SYNTHESIS OF ISOMERICALLY PURE VINYL HALIDES FROM ALKYNES VIA HYDROALUMINATION REACTION
ZWEIFEL, G
WHITNEY, CC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (11) : 2753 - &
[10] Zweifel G., 1967, J AM CHEM SOC, V89, P3652, DOI [10.1021/ja00990a061, DOI 10.1021/JA00990A061]

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