Issue 9, 2007
From the journal:

Organic & Biomolecular Chemistry

Palladium-catalyzed sequential one-pot reaction of aryl bromides with O-homoallylhydroxylamines: synthesis of N-aryl-β-amino alcohols†

Jinsong Peng,ab   Dahong Jiang,ab   Wenqing Lina  and  Yuanwei Chen*a  

* Corresponding authors

a Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, China
E-mail: chenyw@cioc.ac.cn

b Graduate School of Chinese Academy of Sciences, Beijing, China

Abstract

The palladium-catalyzed sequential one-pot N-arylation–carbo-amination–C-arylation of O-homoallylhydroxylamines with two different aryl bromides provides rapid entry to differentially arylated N-aryl-3-arylmethylisoxazolidines in good yields with excellent diastereoselectivity. The obtained isoxazolidines can be reductively cleaved to cis-N-aryl-β-amino alcohols in short times and in high yields at room temperature.

Graphical abstract: Palladium-catalyzed sequential one-pot reaction of aryl bromides with O-homoallylhydroxylamines: synthesis of N-aryl-β-amino alcohols

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Article information

DOI
https://doi.org/10.1039/B701509G
Article type
Paper
Submitted
31 Jan 2007
Accepted
06 Mar 2007
First published
21 Mar 2007

Org. Biomol. Chem., 2007,5, 1391-1396

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Palladium-catalyzed sequential one-pot reaction of aryl bromides with O-homoallylhydroxylamines: synthesis of N-aryl-β-amino alcohols

J. Peng, D. Jiang, W. Lin and Y. Chen, Org. Biomol. Chem., 2007, 5, 1391 DOI: 10.1039/B701509G

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