Convenient synthesis of protected primary amines from nitriles

被引：70

作者：

Caddick, S ^{[1
]}

Haynes, AKD

Judd, DB

Williams, MRV

机构：

[1] Univ Sussex, Chem Lab, Brighton BN1 9QJ, E Sussex, England

[2] Glaxo Wellcome Med Res Ctr, Lead Design, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 18期

关键词：

dimerisation; nickel boride; nitriles; reduction;

D O I：

10.1016/S0040-4039(00)00410-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Investigations into the use of nickel chloride and sodium borohydride for the reduction of nitriles showed the secondary amine dimers to be the major products under normal conditions. The addition of a suitable trapping agent, such as di-tert-butyl dicarbonate, allowed the isolation of the protected primary amines. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：3513 / 3516

页数：4

共 26 条

[1] ENANTIOSPECIFIC SYNTHESIS OF D-ALPHA,OMEGA-DIAMINOALKANOIC ACIDS [J].

BEAULIEU, PL ;

SCHILLER, PW .

TETRAHEDRON LETTERS, 1988, 29 (17) :2019-2022

[2] POTENTIAL GLYCOSIDASE INHIBITORS - SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO DERIVATIVES OF D-GLUCITOL, D-XYLITOL AND L-XYLITOL, D-ALLITOL AND L-ALLITOL, D-TALITOL AND L-TALITOL, AND D-GULITOL [J].

BUCHANAN, JG ;

LUMBARD, KW ;

STURGEON, RJ ;

THOMPSON, DK ;

WIGHTMAN, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03) :699-706

[3] THE CHEMISTRY OF NATURALLY-OCCURRING POLYAMINES .2. A TOTAL SYNTHESIS OF THERMOSPERMINE [J].

CHANTRAPROMMA, K ;

MCMANIS, JS ;

GANEM, B .

TETRAHEDRON LETTERS, 1980, 21 (26) :2475-2476

[4] Synthesis and x-ray crystal structure of (S)-9-hydroxymethyl-1,5-diazabicyclo[4.3.0]non-5-ene, an enantiopure DBN-analogue [J].

Dijkink, J ;

Eriksen, K ;

Goubitz, K ;

vanZanden, MNA ;

Hiemstra, H .

TETRAHEDRON-ASYMMETRY, 1996, 7 (02) :515-524

[5]

ECHVARREN AM, 1991, J ORG CHEM, V56, P452

[6] SYNTHETICALLY USEFUL REACTIONS WITH METAL BORIDE AND ALUMINIDE CATALYSTS [J].

GANEM, B ;

OSBY, JO .

CHEMICAL REVIEWS, 1986, 86 (05) :763-780

[7] THE MECHANISM OF SODIUM-BOROHYDRIDE COBALTOUS CHLORIDE REDUCTIONS [J].

HEINZMAN, SW ;

GANEM, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (24) :6801-6802

[8]

ITO K, 1979, J ORG CHEM, V44, P1014

[9]

KANO S, 1980, SYNTHESIS-STUTTGART, P695

[10]

LU Y, 1990, TETRAHEDRON-ASYMMETR, V1, P707, DOI 10.1016/S0957-4166(00)82379-4

← 1 2 3 →