Synthesis of highly enantio-enriched allylsilanes via palladium-catalyzed intramolecular bis-silylation. Determination of the enantiomeric excesses through regio- and stereoselective hydroboration with 9-BBN

被引：20

作者：

Suginome, M ^{[1
]}

Iwanami, T ^{[1
]}

Matsumoto, A ^{[1
]}

Ito, Y ^{[1
]}

机构：

[1] KYOTO UNIV,GRAD SCH ENGN,DEPT SYNTHET CHEM & BIOL CHEM,KYOTO 60601,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(97)00073-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Highly enantio-enriched (E)-allylsilanes were synthesized by palladium-catalyzed intramolecular bis-silylation of chiral allyl alcohols and subsequent Peterson-type elimination with organolithium reagents. The enantiomeric excesses of the allylsilanes were determined after hydroboration with 9-BBN followed by oxidation, revealing remarkably high stereospecificity for the present synthesis. (C) 1997 Elsevier Science Ltd.

引用

页码：859 / 862

页数：4

共 2 条

[1] Stereoselective synthesis of highly enantioenriched (E)-allylsilanes by palladium-catalyzed intramolecular bis-silylation:: 1,3-chirality transfer and enantioenrichment via dimer formation
Suginome, M
Iwanami, T
Ohmori, Y
Matsumoto, A
Ito, Y
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (10) : 2954 - 2965
[2] Highly regio- and stereoselective synthesis of allylsilanes via palladium-catalyzed reductive metallation of allylic phosphates with a SmI2-HMPA system. Stereochemical aspect of the tandem electron transfer process in allylic systems
Hanamoto, T
Sugino, A
Kikukawa, T
Inanaga, J
[J]. BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1997, 134 (3-4): : 391 - 394

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