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

نویسندگان

  • Shao-Feng Wu
  • Xiao Zheng
  • Yuan-Ping Ruan
  • Pei-Qiang Huang
چکیده

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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عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 7 14  شماره 

صفحات  -

تاریخ انتشار 2009