Catalytic asymmetric synthesis of piperidines from pyrrolidine: concise synthesis of L-733,060.

Julia L Bilke, Stephen P Moore, Peter O'Brien, John Gilday

Department of Chemistry, University of York, Heslington, York YO10 5DD, United Kingdom.

Organic letters 2009 May 7

filter terms:

Catalytic asymmetric deprotonation-aldehyde trapping-ring expansion from a 5- to a 6-ring delivers a concise route to each stereoisomer of beta-hydroxy piperidines starting from N-Boc pyrrolidine. The methodology is utilized in a 5-step catalytic asymmetric synthesis of the neorokinin-1 receptor antagonist, (+)-L-733,060.

Citation

Julia L Bilke, Stephen P Moore, Peter O'Brien, John Gilday. Catalytic asymmetric synthesis of piperidines from pyrrolidine: concise synthesis of L-733,060. Organic letters. 2009 May 7;11(9):1935-8