Enantioselective reduction of ketones by borane catalysed by oxazaphospholidine oxides

被引：40

作者：

Chiodi, O ^{[1
]}

Fotiadu, F ^{[1
]}

Sylvestre, M ^{[1
]}

Buono, G ^{[1
]}

机构：

[1] UNIV AIX MARSEILLE 3,FAC SCI & TECH ST JEROME,ENSSPICAM,CNRS,LAB REACT & CATALYSE,F-13397 MARSEILLE 20,FRANCE

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 01期

关键词：

D O I：

10.1016/0040-4039(95)02078-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New enantioselective catalysts for the asymmetric reduction of ketones by borane are described. Easily prepared by oxidation of chiral oxazaphospholidines, these compounds increase sensitively the reduction rate of numerous ketones and induce ee's up to 94% in the case of the 2-chloroacetophenone.

引用

页码：39 / 42

页数：4

共 18 条

[1] ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY A CHIRAL OXAZAPHOSPHOLIDINE BORANE COMPLEX [J].

BRUNEL, JM ;

PARDIGON, O ;

FAURE, B ;

BUONO, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (03) :287-288

[2] ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY A CHIRAL OXAZAPHOSPHOLIDINE BORANE COMPLEX [J].

BUONO, G ;

BRUNEL, JM ;

FAURE, B ;

PARDIGON, O .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1993, 75 (1-4) :43-46

[3] NEW CATALYSTS CONTAINING AN N-P=O STRUCTURAL UNIT FOR THE ASYMMETRIC REDUCTION OF KETONES [J].

BURNS, B ;

STUDLEY, JR ;

WILLS, M .

TETRAHEDRON LETTERS, 1993, 34 (44) :7105-7106

[4] STEREOELECTRONIC REQUIREMENTS FOR A NEW CLASS OF ASYMMETRIC KETONE REDUCTION CATALYSTS CONTAINING AN N-P=O STRUCTURAL UNIT [J].

BURNS, B ;

KING, NP ;

STUDLEY, JR ;

TYE, H ;

WILLS, M .

TETRAHEDRON-ASYMMETRY, 1994, 5 (05) :801-804

[5] 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

[6] 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

[7] 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

[8]

CROS P, 1987, NEW J CHEM, V11, P573

[9]

DECLOUX A, 1993, CHEM REV, V93, P763

[10] ASYMMETRIC REDUCTION OF AROMATIC KETONES WITH CHIRAL ALKOXY-AMINE-BORANE COMPLEXES [J].

HIRAO, A ;

ITSUNO, S ;

NAKAHAMA, S ;

YAMAZAKI, N .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (07) :315-317

← 1 2 →