STEREOCONTROLLED SYNTHESIS OF 1,3,5-TRIOLS BY TANDEM HYDROBORATION CARBONYL REDUCTION

被引：22

作者：

HARADA, T

IMANAKA, S

OHYAMA, Y

MATSUDA, Y

OKU, A

机构：

[1] Department of Chemistry, Kyoto Institute of Technology Matsugasaki, Sakyo-ku, Kyoto

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 39期

关键词：

D O I：

10.1016/0040-4039(92)89037-D

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly convergent method for the stereoselective synthesis of 1,3,5-triol frameworks has been developed by utilizing a tandem hydroboration/carbonyl reduction of beta-silyl-gamma,delta-unsaturated ketones 2 with thexylborane.

引用

页码：5807 / 5810

页数：4

共 9 条

[1]

ALEXAKIS A, 1990, ORG SYNTH COLL, V7, P290

[2]

BASSINDALE AR, 1989, CHEM ORGANIC SILICON, P830

[3]

CORRIU RJP, 1989, CHEM ORGANIC SILICON, P1241

[4] REMARKABLE BRONSTED TYPE CORRELATION FOR BASE CLEAVAGE OF CARBON-SILICON BONDS - KINETIC ISOTOPE-EFFECTS FOR INTERACTION OF CARBANIONS WITH METHANOL [J].

EABORN, C ;

WALTON, DRM ;

SECONI, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (23) :937-939

[5] THE SYNTHESIS OF ALPHA-BETA-UNSATURATED KETONES FROM BETA-SILYLENONES AND BETA-SILYLYNONES [J].

FLEMING, I ;

PERRY, DA .

TETRAHEDRON, 1981, 37 (23) :4027-4034

[6]

FLEMING I, 1988, TETRAHEDRON LETT, V29, P2027

[7] REMOTE STEREOCONTROL BY UTILIZING INTRAMOLECULAR CARBONYL REDUCTION WITH BORANES [J].

HARADA, T ;

MATSUDA, Y ;

IMANAKA, S ;

OKU, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (22) :1641-1643

[8] NUCLEOPHILIC DISPLACEMENT OF METHIDE FROM SILICON - STERIC COMPRESSION OF GEMINAL TRIMETHYLSILYL GROUPS [J].

KIRMSE, W ;

SOLLENBOHMER, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (12) :774-775

[9] SILAFUNCTIONAL COMPOUNDS IN ORGANIC-SYNTHESIS .34. NEW ROUTES TO REGIOSELECTIVELY MONO-PROTECTED 1,3-DIOLS FROM ALLYL AND HOMOALLYL ALCOHOLS VIA INTRAMOLECULAR HYDROSILATION [J].

TAMAO, K ;

YAMAUCHI, T ;

ITO, Y .

CHEMISTRY LETTERS, 1987, (01) :171-174

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