Enantioselective Ring Expansion of Prolinols: An Efficient and Short Synthesis of 2-Phenylpiperidin-3-ol Derivatives and 3-Hydroxypipecolic Acids

Abstract A very short route to 2-phenylpiperidin-3-ol derivatives and 3-hydroxypipecolic acids is described. The approach uses two key steps: a one-pot reduction/Grignard addition sequence applied to alkyl proline esters and a ring expansion applied to the corresponding prolinols.

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Bibliographic Details
Published in:Synlett 2009-08, Vol.2009 (13), p.2157-2161
Main Authors: Cochi, Anne, Burger, Benjamin, Navarro, Cristina, Gomez Pardo, Domingo, Cossy, Janine, Zhao, Yang, Cohen, Theodore
Format: Article
Language:English
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Summary:Abstract A very short route to 2-phenylpiperidin-3-ol derivatives and 3-hydroxypipecolic acids is described. The approach uses two key steps: a one-pot reduction/Grignard addition sequence applied to alkyl proline esters and a ring expansion applied to the corresponding prolinols.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0029-1217568