Gold-catalyzed intramolecular hydroamination of allenes: a case of chirality transfer

被引：88

作者：

Patil, Nitin T. ^{[1
]}

Lutete, Leopold Mpaka ^{[1
]}

Nishina, Naoko ^{[1
]}

Yamamoto, Yoshinori ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 27期

关键词：

allene; gold catalyst; hydroamination; nitrogen heterocycles; chirality transfer;

D O I：

10.1016/j.tetlet.2006.04.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hydroamination of allenes proceeded smoothly in the presence of gold catalysts to give the corresponding 2-vinyl pyrrolidines and piperidines in high yields. The reaction is very efficient and can be carried out with only 1-5 mol % catalyst at room temperature and under extremely mild conditions. As an example of chirality transfer, it is shown that aminoallene la (96% ee), synthesized from (S)-(-)-1-octyn-3-ol, was converted into the corresponding pyrrolidine 2a (94% ee) in 99% yield. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4749 / 4751

页数：3

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