Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: Application of an organocatalytic direct vinylogous aldol reaction

Sunil V. Pansare; Eldho K. Paul

doi:10.1039/C2OB06644K

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Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: Application of an organocatalytic direct vinylogous aldol reaction†

Sunil V. Pansare*^a and Eldho K. Paul^a

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^a Department of Chemistry, Memorial University, St. John's, Newfoundland, Canada
E-mail: spansare@mun.ca

Abstract

The γ-butenolide obtained from an organocatalyzed, direct vinylogous aldol reaction of γ-crotonolactone and benzaldehyde serves as the key starting material in the expedient synthesis of a 3-hydroxy-2-phenyl piperidine intermediate which is converted to the target 2,3-disubstituted piperidines.

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Article information

DOI: https://doi.org/10.1039/C2OB06644K
Article type: Paper
Submitted: 27 Sep 2011
Accepted: 14 Dec 2011
First published: 21 Dec 2011

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Org. Biomol. Chem., 2012,10, 2119-2125

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Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: Application of an organocatalytic direct vinylogous aldol reaction

S. V. Pansare and E. K. Paul, Org. Biomol. Chem., 2012, 10, 2119 DOI: 10.1039/C2OB06644K

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Organic & Biomolecular Chemistry

Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: Application of an organocatalytic direct vinylogous aldol reaction†

Abstract

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Synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid: Application of an organocatalytic direct vinylogous aldol reaction

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