First evidence for the use of polyamines as nucleophiles in a regioselective palladium-catalyzed allylic amination reaction

被引：5
|
作者：
Pieri, Cyril [1 ]
Combes, Sebastien [1 ]
Brunel, Jean Michel [1 ]
机构：
[1] Aix Marseille Univ, Inst Paoli Calmettes, CNRS UMR7258, CRCM,UM 105,Inserm U1068, F-13009 Marseille, France
来源：
TETRAHEDRON | 2014年 / 70卷 / 51期
关键词：
Palladium catalysis; Allylic amination; Polyamines; Stereoselective reaction; GRAM-NEGATIVE BACTERIA; CARBONYL-COMPOUNDS; GENERAL BASE; ALKYLATION; AMINES; SUBSTITUENT; SQUALAMINE; MECHANISMS; RATES;
D O I：
10.1016/j.tet.2014.10.019
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium-catalyzed reaction of unsymmetrical allylic electrophiles with polyamines gives rise to regioisomeric allylic polyamines. An original catalytic procedure providing an efficient method for the regioselective synthesis of new classes of polyamino derivatives of biological interest is reported. Based on experimental considerations, a mechanistic rationale involving a thermodynamically controlled isomerization of the initially formed branched product is proposed to account for the total regioselectivity observed. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9718 / 9725
页数：8
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