Stereocontrolled reductive amination of 3-hydroxy ketones.

被引：30

作者：

Haddad, M

Dorbais, J

Larcheveque, M

机构：

[1] Lab. de Synt. Organique Associe A., ENSCP, Paris Cedex 05

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 34期

关键词：

D O I：

10.1016/S0040-4039(97)01349-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

syn-1,3-Aminoalcohols are synthesized in high diastereomeric excess by reductive amination of 3-hydroxyketones with sodium cyanoborohydride in the presence of benzylamine. (C) 1997 Published by Elsevier Science Ltd.

引用

页码：5981 / 5984

页数：4

共 14 条

[1] REDUCTIVE AMINATION OF ALDEHYDES AND KETONES BY USING SODIUM TRIACETOXYBOROHYDRIDE [J].

ABDELMAGID, AF ;

MARYANOFF, CA ;

CARSON, KG .

TETRAHEDRON LETTERS, 1990, 31 (39) :5595-5598

[2]

BARLUENGA J, 1990, SYNLETT, P463

[3] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].

EVANS, DA ;

CHAPMAN, KT ;

CARREIRA, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578

[4]

HASHIGUCHI S, 1992, SYNTHESIS-STUTTGART, P403

[5] INTRAMOLECULAR AMIDOALKYLATION OF CHIRAL IMINIUM IONS - STEREOSELECTIVE SYNTHESIS OF SYN-1,3-AMINOALCOHOLS [J].

HIOKI, H ;

OKUDA, M ;

MIYAGI, W ;

ITO, S .

TETRAHEDRON LETTERS, 1993, 34 (38) :6131-6134

[6] CARBAMATE-MEDIATED FUNCTIONALIZATION OF UNSATURATED ALCOHOLS .3. INTRAMOLECULAR MICHAEL ADDITION OF O-CARBAMATES TO ALPHA,BETA-UNSATURATED ESTERS - A NEW DIASTEREOSELECTIVE AMINATION IN AN ACYCLIC SYSTEM [J].

HIRAMA, M ;

SHIGEMOTO, T ;

YAMAZAKI, Y ;

ITO, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (06) :1797-1798

[7]

JAGER V, 1978, TETRAHEDRON LETT, P3133

[8]

JAGER V, 1980, LIEBIGS ANN CHEM, P101

[9] STEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES TO 1,3-DIOLS - HIGHLY SELECTIVE 1,3-ASYMMETRIC INDUCTION VIA BORON CHELATES [J].

NARASAKA, K ;

PAI, FC .

TETRAHEDRON, 1984, 40 (12) :2233-2238

[10] STEREOSELECTIVE PREPARATION OF ACYCLIC SYN-BETA-AMINO ALCOHOLS FROM BETA-HYDROXY KETONES VIA THE CORRESPONDING O-BENZYL OXIMES [J].

NARASAKA, K ;

UKAJI, Y ;

YAMAZAKI, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (02) :525-533

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