Enantioselective synthesis of new C-2-symmetric ferrocenylalkylamines via sonochemical amination of 1-ferrocenylalkyl acetates

被引：42

作者：

Woltersdorf, M ^{[1
]}

Kranich, R ^{[1
]}

Schmalz, HG ^{[1
]}

机构：

[1] TECH UNIV BERLIN,INST ORGAN CHEM,D-10623 BERLIN,GERMANY

来源：

TETRAHEDRON | 1997年 / 53卷 / 21期

关键词：

D O I：

10.1016/S0040-4020(97)00407-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of four new C-2-symmetric ferrocenylalkylamines, (R,R)-bis(1-ferrocenyl-ethyl)-amine (5), (R,R)-N,N'-bis-(1-ferrocenyl-ethyl)-ethane-1,2-diamine (6), (R,R)-2,6-diferrocenyl-piperidine (7a), and (R,R)-2,5-diferrocenyl-pyrrolidine (7b) is described. The syntheses are based on the enantioselective, oxazaborolidine catalyzed borane reduction of acylferrocenes followed by S(n)1 amination, which can be accelerated by ultrasound, as shown for the preparation of (R)-1-ferrocenyl-ethylamine (15) in greatly improved yield. (C) 1997 Elsevier Science Ltd.

引用

页码：7219 / 7230

页数：12

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