Royal Society of Chemistry, Organic and Biomolecular Chemistry, 14(7), p. 2967, 2009
DOI: 10.1039/b906224f
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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. ; NSF of China [20832005]; Innovative Research Team in Science & Technology (University) in Fujian Province and the Program for New Century Excellent Talents in Xiamen University