STEREOSELECTIVE SYNTHESIS OF BOTH GEOMETRIC ISOMERS OF GAMMA-(TRIMETHYLSILYL)ALLYLBORANES AND THE DIASTEREOSELECTIVE CONDENSATIONS WITH ALDEHYDES

被引：19

作者：

GU, YG ^{[1
]}

WANG, KK ^{[1
]}

机构：

[1] W VIRGINIA UNIV,DEPT CHEM,MORGANTOWN,WV 26506

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 26期

关键词：

ALLENYLSILANES; HYDROBORATION; GAMMA-(TRIMETHYLSILYL)ALLYLBORANES; CONDENSATION WITH ALDEHYDES; HYDROXYALLYLSILANES;

D O I：

10.1016/0040-4039(91)80678-Y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydroboration of allenylsilanes 1 produces the Z isomers 10 as the kinetic product, leading to hydroxyallylsilanes 15 after condensation with hexanal, whereas the E isomers 4 and 12 are thermodynamically more stable, affording 9 predominantly.

引用

页码：3029 / 3032

页数：4

共 6 条

[1] Fleming I., 1989, ORG REACTIONS, V37, P57
[2] STEREOSPECIFIC OLEFIN-FORMING ELIMINATION-REACTIONS OF BETA-HYDROXYALKYLSILANES
HUDRLIK, PF
PETERSON, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) : 1464 - 1468
[3] 9-BORABICYCLO[3.3.1]NONANE AS A HIGHLY SELECTIVE REDUCING AGENT FOR FACILE CONVERSION OF ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES TO CORRESPONDING ALLYLIC ALCOHOLS IN PRESENCE OF OTHER FUNCTIONAL GROUPS
KRISHNAMURTHY, S
BROWN, HC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (12) : 1864 - 1865
[4] STEREOSELECTIVE SYNTHESIS OF ALL 4 GEOMETRIC ISOMERS OF INTERNAL 1,3-BUTADIENES BY THE CONDENSATION REACTION OF ALDEHYDES WITH THE GAMMA-TRIMETHYLSILYL-SUBSTITUTED ALLYLBORANES
WANG, KK
GU, YG
LIU, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4424 - 4431
[5] WANG KK, IN PRESS J ORG CHEM
[6] SYNTHESIS OF 1,4-DISUBSTITUTED (E,Z)-1,3-DIENES FROM LITHIUM DICYCLOHEXYL(TRANS-1-ALKENYL)(1-ALKYNYL)BORATES
ZWEIFEL, G
BACKLUND, SJ
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 156 (01) : 159 - 170

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