Synthesis of 3-alkenylamines, 4-alkenylamines and 3-allenylamines via a transamination procedure

被引：18

作者：

DeKimpe, N

DeSmaele, D

Hofkens, A

Dejaegher, Y

Kesteleyn, B

机构：

[1] Department of Organic Chemistry, Fac. of Agric. and Appl. Biol. Sci., University of Gent, B-9000 Gent

来源：

TETRAHEDRON | 1997年 / 53卷 / 31期

关键词：

D O I：

10.1016/S0040-4020(97)00688-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Alkenylamines, 4-alkenylamines and 3-allenylamines were synthesized conveniently by potassium t-butoxide induced transamination of alpha-vinylaldimines, alpha-allylaldimines or alpha-allenylaldimines followed by hydrolysis with aqueous oxalic acid. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：10803 / 10816

页数：14

相关论文

共 28 条

[1] STEREOCONTROLLED SYNTHESIS OF HOMOALLYLIC AMINES USING PHOSPHINE OXIDES AND ISOXAZOLINES [J].

ARMSTRONG, SK ;

WARREN, S ;

COLLINGTON, EW ;

NAYLOR, A .

TETRAHEDRON LETTERS, 1991, 32 (33) :4171-4174

[2]

ARSENSIO G, 1995, J ORG CHEM, V60, P3692

[3] PREPARATION OF SUBSTITUTED 4-PENTENALS [J].

BRANNOCK, KC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (13) :3379-3383

[4] Efficient transamination under mild conditions: Preparation of primary amine derivatives from carbonyl compounds via imine isomerization with catalytic amounts of potassium tert-butoxide [J].

Cainelli, G ;

Giacomini, D ;

Trere, A ;

Boyl, PP .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (15) :5134-5139

[5] The preparation of unsymmetrical secondary aliphatic ammes [J].

Campbell, KN ;

Sommers, AH ;

Campbell, BK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :82-84

[6]

Cheikh R. B., 1983, SYNTHESIS-STUTTGART, P685, DOI DOI 10.1055/S-1983-30473

[7] DEPROTONATION OF TERNARY IMINIUM SALTS [J].

DEYRUP, JA ;

SZABO, WA .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (14) :2048-2052

[8]

DIEFL HK, 1973, TETRAHEDRON LETT, P1273

[9] Efficient synthesis of allylic amines from alpha-aminoalkyl cuprates and enol triflates [J].

Dieter, RK ;

Dieter, JW ;

Alexander, CW ;

Bhinderwala, NS .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :2930-2931

[10] Mechanisms of decomposition of (Z)-2,2,2-trifluoro-1-arylethanediazoates in aqueous media [J].

Finneman, JI ;

Fishbein, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (30) :7134-7138