ENANTIOSELECTIVE REDUCTIONS OF 2-ACYL-1,3-DITHIANES USING THE COREY OXAZABOROLIDINE CATALYST

被引：40

作者：

DENINNO, MP

PERNER, RJ

LIJEWSKI, L

机构：

[1] Neuroscience Research Division, Pharmaceutical Discovery, Dept 47U, Abbott Park

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(00)88503-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective reduction of acyl dithianes has been achieved using the oxazaborolidine catalyst 1b. The dithiane group can then be hydrolyzed to the ketone or removed reductively.

引用

页码：7415 / 7418

页数：4

共 19 条

[1] AN EFFICIENT AND CATALYTICALLY ENANTIOSELECTIVE ROUTE TO (S)-(-)-PHENYLOXIRANE [J].

COREY, EJ ;

SHIBATA, S ;

BAKSHI, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2861-2863

[2] A NEW CHIRAL CATALYST FOR THE ENANTIOSELECTIVE SYNTHESIS OF SECONDARY ALCOHOLS AND DEUTERATED PRIMARY ALCOHOLS BY CARBONYL REDUCTION [J].

COREY, EJ ;

LINK, JO .

TETRAHEDRON LETTERS, 1989, 30 (46) :6275-6278

[3] A NEW SYSTEM FOR CATALYTIC ENANTIOSELECTIVE REDUCTION OF ACHIRAL KETONES TO CHIRAL ALCOHOLS - SYNTHESIS OF CHIRAL ALPHA-HYDROXY ACIDS [J].

COREY, EJ ;

BAKSHI, RK .

TETRAHEDRON LETTERS, 1990, 31 (05) :611-614

[4] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[5] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S ;

CHEN, CP ;

SINGH, VK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926

[6] OXIDATIVE HYDROLYSIS OF 1,3-DITHIANE DERIVATIVES TO CARBONYL COMPOUNDS USING N-HALOSUCCINIMIDE REAGENTS [J].

COREY, EJ ;

ERICKSON, BW .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (23) :3553-&

[7] CARBANIONS OF 1,3-DITHIANES . REAGENTS FOR C-C BOND FORMATION BY NUCLEOPHILIC DISPLACEMENT AND CARBONYL ADDITION [J].

COREY, EJ ;

SEEBACH, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1965, 4 (12) :1075-&

[8] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[9] ENANTIOSELECTIVE SYNTHESIS OF ALPHA-HYDROXYTHIOACETALS BY THE BAKERS-YEAST REDUCTION OF ALPHA-KETOTHIOACETALS [J].

FUJISAWA, T ;

KOJIMA, E ;

ITOH, T ;

SATO, T .

CHEMISTRY LETTERS, 1985, (11) :1751-1754

[10] REACTION BETWEEN VICINAL DIOLS AND HYDROGEN BROMIDE IN ACETIC-ACID - SYNTHESIS OF CHIRAL PROPYLENE-OXIDE [J].

GOLDING, BT ;

HALL, DR ;

SAKRIKAR, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (11) :1214-1220

← 1 2 →