ENANTIOSELECTIVE OXAZABOROLIDINE REDUCTION OF KETONES CONTAINING HETEROATOMS

被引：50

作者：

QUALLICH, GJ

WOODALL, TM

机构：

[1] Process Research and Development, Central Research Division, Pfizer Inc., Groton

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 05期

关键词：

ENANTIOSELECTIVE REDUCTION; OXAZABOROLIDINE; CHIRAL ALCOHOL; CATALYTIC REDUCTION; AMINE-BORANE;

D O I：

10.1016/0040-4039(93)89012-F

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ketones which contain heteroatom, particularly nitrogen, can be enantioselectively and catalytically reduced with chiral oxazaborolidines in the presence of excess borane.

引用

页码：785 / 788

页数：4

共 19 条

[1] REDUCTION OF CARBONYL COMPOUNDS WITH PYRIDINE BORANE [J].

BARNES, RP ;

GRAHAM, JH ;

TAYLOR, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (10) :1561-1562

[2] CHIRAL SYNTHESIS VIA ORGANOBORANES .14. SELECTIVE REDUCTIONS .41. DIISOPINOCAMPHEYLCHLOROBORANE, AN EXCEPTIONALLY EFFICIENT CHIRAL REDUCING AGENT [J].

BROWN, HC ;

CHANDRASEKHARAN, J ;

RAMACHANDRAN, PV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1539-1546

[3] 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

[4] 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

[5] 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

[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]

COREY EJ, 1990, Patent No. 4943635

[9] SYNTHESIS OF OPTICALLY-ACTIVE COMPOUNDS - A LARGE-SCALE PERSPECTIVE [J].

CROSBY, J .

TETRAHEDRON, 1991, 47 (27) :4789-4846

[10] ASYMMETRIC-SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF LY248686 [J].

DEETER, J ;

FRAZIER, J ;

STATEN, G ;

STASZAK, M ;

WEIGEL, L .

TETRAHEDRON LETTERS, 1990, 31 (49) :7101-7104

← 1 2 →