Issue 45, 2009
From the journal:

Chemical Communications

One-pot cross-coupling of N-acyl N,O-acetals with α,β-unsaturated compounds†

Yong-Gang Xiang,‡a   Xiang-Wu Wang,‡a   Xiao Zheng,*bc   Yuan-Ping Ruana  and  Pei-Qiang Huang*a  

* Corresponding authors

a Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. China
E-mail: pqhuang@xmu.edu.cn
Fax: +86-592-2186400

b Department of Pharmaceutical Sciences, Medical College, Xiamen University, Xiamen, Fujian 361005, P. R. China

c Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
E-mail: zxiao@xmu.edu.cn

Abstract

The synergistic action of BF3·OEt2 and SmI2 allowed a series of intermolecular cross-couplings of readily available N-acyl N,O-acetals with α,β-unsaturated compounds to be performed in high yields, which was applied to the stereoselective synthesis of pyrrolizidine alkaloid (+)-xenovenine.

Graphical abstract: One-pot cross-coupling of N-acyl N,O-acetals with α,β-unsaturated compounds

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Article information

DOI
https://doi.org/10.1039/B915488D
Article type
Communication
Submitted
29 Jul 2009
Accepted
23 Sep 2009
First published
13 Oct 2009

Chem. Commun., 2009, 7045-7047

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One-pot cross-coupling of N-acyl N,O-acetals with α,β-unsaturated compounds

Y. Xiang, X. Wang, X. Zheng, Y. Ruan and P. Huang, Chem. Commun., 2009, 7045 DOI: 10.1039/B915488D

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