Structural effects of the oxazaborolidine derived from L-threonine in the reduction of (trifluoroacetyl)biphenyl derivatives with catecholborane

被引：14

作者：

Fujisawa, T ^{[1
]}

Onogawa, Y ^{[1
]}

Shimizu, M ^{[1
]}

机构：

[1] Mie Univ, Dept Chem Mat, Tsu, Mie 5148507, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 33期

关键词：

reduction; oxazaborolidine; L-threonine; (trifluoroacetyl)biphenyl derivatives;

D O I：

10.1016/S0040-4039(98)01237-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reduction of (trifluoroacetyl)biphenyl derivatives with catecholborane as a stoichiometric reductant in the presence of the oxazaborolidine catalyst derived from L-threonine in dichloromethane-toluene at -90 degrees C proceeds to give the corresponding alcohols in high yields with high enantioselectivity: The distinctive feature of this oxazaborolidine exists in the five-membered ring covered with the t-butyldimethylsiloxy group. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：6019 / 6022

页数：4

相关论文

共 41 条

[1] Asymmetric synthesis of (S)-carbinoxamine. New aspects of oxazaborolidine-catalyzed enantioselective carbonyl reduction [J].

Corey, EJ ;

Helal, CJ .

TETRAHEDRON LETTERS, 1996, 37 (32) :5675-5678

[2] A CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF CHIRAL MONOSUBSTITUTED OXIRANES [J].

COREY, EJ ;

HELAL, CJ .

TETRAHEDRON LETTERS, 1993, 34 (33) :5227-5230

[3] 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

[4] A MECHANISTIC AND STRUCTURAL-ANALYSIS OF THE BASIS FOR HIGH ENANTIOSELECTIVITY IN THE OXAZABOROLIDINE-CATALYZED REDUCTION OF TRIHALOMETHYL KETONES BY CATECHOLBORANE [J].

COREY, EJ ;

LINK, JO ;

BAKSHI, RK .

TETRAHEDRON LETTERS, 1992, 33 (47) :7107-7110

[5] A GENERAL, CATALYTIC, AND ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

COREY, EJ ;

LINK, JO .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1906-1908

[6] 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

[7] A CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF DENOPAMINE, A USEFUL DRUG FOR CONGESTIVE-HEART-FAILURE [J].

COREY, EJ ;

LINK, JO .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :442-444

[8] ENANTIOSELECTIVE AND PRACTICAL SYNTHESES OF R-FLUOXETINE AND S-FLUOXETINE [J].

COREY, EJ ;

REICHARD, GA .

TETRAHEDRON LETTERS, 1989, 30 (39) :5207-5210

[9] An efficient catalytic stereoselective route to a key intermediate for the synthesis of the long-lived PGI(2) analog ZK 96480 (Cicaprost(TM)) [J].

Corey, EJ ;

Helal, CJ .

TETRAHEDRON LETTERS, 1997, 38 (43) :7511-7514

[10] REMARKABLY EFFECTIVE AND SIMPLE SYNTHESES OF ENANTIOMERICALLY PURE SECONDARY CARBINOLS FROM ACHIRAL KETONES [J].

COREY, EJ ;

CHENG, XM ;

CIMPRICH, KA ;

SARSHAR, S .

TETRAHEDRON LETTERS, 1991, 32 (47) :6835-6838

← 1 2 3 4 5 →