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  • Title: A new approach to 3-hydroxyprolinol derivatives by samarium diiodide-mediated reductive coupling of chiral nitrone with carbonyl compounds.
    Author: Wu SF, Zheng X, Ruan YP, Huang PQ.
    Journal: Org Biomol Chem; 2009 Jul 21; 7(14):2967-75. PubMed ID: 19582307.
    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.
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