Stereoselective synthesis of (2 S,3 S)-3-hydroxy-2-phenylpiperidine from d-mannitol

A novel stereoselective synthesis of N-Boc-(2 S,3 S)-3-hydroxy-2-phenylpiperidine was achieved from d-mannitol involving the highly stereoselective addition of phenyl Grignard to an allyl imine (de >98%) and ring-closing metathesis (RCM) in the key steps.

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2009-02, Vol.20 (2), p.198-201
Main Authors: Venkataiah, Mallam, Venkateswara Rao, B., Fadnavis, Nitin W.
Format: Article
Language:English
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Summary:A novel stereoselective synthesis of N-Boc-(2 S,3 S)-3-hydroxy-2-phenylpiperidine was achieved from d-mannitol involving the highly stereoselective addition of phenyl Grignard to an allyl imine (de >98%) and ring-closing metathesis (RCM) in the key steps.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2008.12.005