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Issue 14, 2009
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A new approach to 3-hydroxyprolinol derivatives by samarium diiodide-mediated reductive coupling of chiral nitrone with carbonyl compounds

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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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Supplementary files

Article information


Submitted
30 Mar 2009
Accepted
27 Apr 2009
First published
02 Jun 2009

Org. Biomol. Chem., 2009,7, 2967-2975
Article type
Paper

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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