General route to a new class of homochiral azetidine-derived 1,2-diamines

被引：18

作者：

Couty, F ^{[1
]}

Evano, G

Prim, D

Marrot, J

机构：

[1] Univ Versailles, CNRS, UMR 8086, Lab SIRCOB, F-78035 Versailles, France

[2] Univ Versailles, CNRS, UMR 8037, Inst Lavoisier, F-78035 Versailles, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 18期

关键词：

aminonitriles; azetidines; vicinal diamines;

D O I：

10.1002/ejoc.200400233

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short access to novel azetidine-derived anti-1,2-diamines starting from easily accessible 2-cyanoazetidines has been developed. A one-pot sequence, including a nucleophilic addition and reduction of the resulting imine, allows for a diastereoselective synthesis of variously substituted diamines. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

引用

页码：3893 / 3897

页数：5

共 39 条

[1] A straightforward synthesis of enantiopure 2-cyano azetidines from β-amino alcohols [J].

Agami, C ;

Couty, F ;

Evano, G .

TETRAHEDRON-ASYMMETRY, 2002, 13 (03) :297-302

[2] Synthesis of α-substituted allylic amines via a modified bruylants reaction [J].

Agami, C ;

Couty, F ;

Evano, G .

ORGANIC LETTERS, 2000, 2 (14) :2085-2088

[3] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene [J].

Alexakis, A ;

Andrey, O .

ORGANIC LETTERS, 2002, 4 (21) :3611-3614

[4]

Alexakis A, 2000, ANGEW CHEM INT EDIT, V39, P4093, DOI 10.1002/1521-3773(20001117)39:22<4093::AID-ANIE4093>3.0.CO

[5]

2-R

[6] Structure of the diamine-Rh(I) precursor in the asymmetric hydride transfer reduction of ketones: A theoretical and experimental approach [J].

Bernard, M ;

Guiral, V ;

Delbecq, F ;

Fache, F ;

Sautet, P ;

Lemaire, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (07) :1441-1446

[7] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].

Betancort, JM ;

Barbas, CF .

ORGANIC LETTERS, 2001, 3 (23) :3737-3740

[8] SYNTHESIS OF OPTICALLY-ACTIVE ETHANOLAMINES [J].

BRUSSEE, J ;

DOFFERHOFF, F ;

KRUSE, CG ;

VANDERGEN, A .

TETRAHEDRON, 1990, 46 (05) :1653-1658

[9] An efficient and cost-effective synthesis of 2-phenyl-3-aminopyridine [J].

Caron, S ;

Massett, SS ;

Bogle, DE ;

Castaldi, MJ ;

Braish, TF .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (03) :254-256

[10] Regio- and stereoselective C-2 and C-3 cleavage of 2-(1-aminoalkyl)aziridines with alcohols, carboxylic acids, and sodium iodide [J].

Concellón, JM ;

Riego, E ;

Suárez, JR .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9242-9246

← 1 2 3 4 →