Xiao Zheng, Chen‐Guo Feng, Jian-Liang Ye
Jan 21, 2005
Citations
0
Influential Citations
30
Citations
Journal
Organic letters
Abstract
The N,O-diprotected chiral nonracemic 2-pyridyl 3-pyrrolidinol-2-yl sulfide 5a undergoes efficient SmI(2) mediated reduction to give the N,O-diprotected 3-pyrrolidinol 2-carbanion intermediate D, which reacted under Barbier-type conditions with ketones and aldehydes to afford the protected N-alpha-hydroxyalkyl-3-pyrrolidines 10b-h with excellent diastereoselectivity at the newly formed chiral center in the pyrrolidine ring. Application of the present method led to the formal asymmetric syntheses of (2R,3S)-2-hydroxymethyl-3-pyrrolidinol (2) and (2S,3S)-3-hydroxyproline (12). [reaction: see text]