Issue 14, 2009
From the journal:

Organic & Biomolecular Chemistry

A new approach to 3-hydroxyprolinol derivatives by samarium diiodide-mediated reductive coupling of chiral nitrone with carbonyl compounds†

Shao-Feng Wu,a   Xiao Zheng,*a   Yuan-Ping Ruana  and  Pei-Qiang Huang*a  

* Corresponding authors

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

Abstract

A flexible diastereoselective approach to trans-(3S)-hydroxyprolinol derivatives is described, which is based on the samarium diiodide-mediated reductive coupling of the chiral 1-pyrroline N-oxide (nitrone)(S)-10 with carbonyl compounds. The reductive hydroxyalkylation of nitrone 10 with ketones and aromatic aldehydes is highly diastereoselective in establishing the C-2 chiral center of the pyrrolidine ring.

Graphical abstract: A new approach to 3-hydroxyprolinol derivatives by samarium diiodide-mediated reductive coupling of chiral nitrone with carbonyl compounds

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Article information

DOI
https://doi.org/10.1039/B906224F
Article type
Paper
Submitted
30 Mar 2009
Accepted
27 Apr 2009
First published
02 Jun 2009

Org. Biomol. Chem., 2009,7, 2967-2975

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A new approach to 3-hydroxyprolinol derivatives by samarium diiodide-mediated reductive coupling of chiral nitrone with carbonyl compounds

S. Wu, X. Zheng, Y. Ruan and P. Huang, Org. Biomol. Chem., 2009, 7, 2967 DOI: 10.1039/B906224F

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