NOVEL SYNTHESIS OF SYN-ALPHA,BETA-EPOXY ALCOHOLS BY DIASTEREOSELECTIVE CARBONYL REDUCTION OF ALPHA,BETA-EPOXY KETONES

被引：15

作者：

KAWAKAMI, T ^{[1
]}

SHIBATA, I ^{[1
]}

BABA, A ^{[1
]}

MATSUDA, H ^{[1
]}

SONODA, N ^{[1
]}

机构：

[1] OSAKA UNIV, FAC ENGN, DEPT APPL CHEM, SUITA, OSAKA 565, JAPAN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(00)78454-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel tin hydride reagent, Bu(3)SnH-Bu(4)NCN, reduced alpha,beta-epoxy ketones to the corresponding syn-alpha,beta-epoxy alcohols in high diastereoselectivities.

引用

页码：8625 / 8626

页数：2

共 20 条

[1] A NEW PREPARATIVE ROUTE TO CHIRAL 2,3-EPOXY-1,4-BUTANEDIOLS [J].

AOYAMA, Y ;

URABE, H ;

SATO, F .

TETRAHEDRON LETTERS, 1991, 32 (46) :6731-6734

[2]

BANFI S, 1983, SYN COMMUN, P901

[3]

CASTAING MD, 1986, J ORG CHEM, V51, P1672

[4] ASYMMETRIC INDUCTION AND [2+1] CYCLOADDITIONS .3. DIASTEREOSELECTIVE EPOXIDATIONS OF SECONDARY ALPHA ETHYLENIC ALCOHOLS AND STEREODIRECTED SYNTHESES OF ALPHA EPOXY ALCOHOLS [J].

CHAUTEMPS, P ;

PIERRE, JL .

TETRAHEDRON, 1976, 32 (05) :549-557

[5]

Cherest M., 1968, TETRAHEDRON LETT, V18, P2199

[6] STEREOSELECTIVE REDUCTION OF ALPHA,BETA-EPOXY KETONES INTO ERYTHRO-ALPHA,BETA-EPOXY ALCOHOLS WITH SODIUM-BOROHYDRIDE IN THE PRESENCE OF CALCIUM-CHLORIDE [J].

FUJII, H ;

OSHIMA, K ;

UTIMOTO, K .

CHEMISTRY LETTERS, 1992, (06) :967-970

[7] FLUORIDE-ION CATALYZED REDUCTION OF ALDEHYDES AND KETONES WITH HYDROSILANES - SYNTHETIC AND MECHANISTIC ASPECTS AND AN APPLICATION TO THE THREO-DIRECTED REDUCTION OF ALPHA-SUBSTITUTED ALKANONES [J].

FUJITA, M ;

HIYAMA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5405-5415

[8] TETRABUTYLAMMONIUM DIFLUOROTRIPHENYLSTANNATE AS A NEW ANHYDROUS SYNTHETIC EQUIVALENT TO TBAF [J].

GINGRAS, M .

TETRAHEDRON LETTERS, 1991, 32 (50) :7381-7384

[9] EPOXIDATION OF ALLYL AND HOMOALLYL TRIMETHYLSILYL ETHERS WITH TERT-BUTYLDIOXYTRIMETHYLSILANE AND SILICON LEWIS ACID VANADIUM CATALYST [J].

HIYAMA, T ;

OBAYASHI, M .

TETRAHEDRON LETTERS, 1983, 24 (04) :395-398

[10] CHEMOSELECTIVE AND STEREOSELECTIVE CARBONYL REDUCTION OF ALPHA,BETA-EPOXY KETONES BY BU2SNFH [J].

KAWAKAMI, T ;

SHIBATA, I ;

BABA, A ;

MATSUDA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7608-7609

← 1 2 →