A Facile Asymmetric Synthesis of Either Enantiomer of 2-Substituted Pyrrolidines

L Rajender Reddy, SG Das, Y Liu…

Index: Reddy, Leleti Rajender; Das, Sonia G.; Liu, Yugang; Prashad, Mahavir Journal of Organic Chemistry, 2010 , vol. 75, # 7 p. 2236 - 2246

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Citation Number: 34

Abstract

A new and general method for asymmetric synthesis of either enantiomer of 2-substituted pyrrolidines from a single starting material is described. Reductive cyclization of (SS)-γ- chloro-N-tert-butanesulfinyl ketimines with LiBHEt3 in THF at− 78 to 23° C afforded (SS, R)- N-tert-butanesulfinyl-2-substituted pyrrolidines in excellent yields (88− 98%) and with high diastereoselectivity (99: 1). The diastereoselectivity is controlled effectively by the choice ...