Concise enantioselective synthesis of (2S,3S)-3-hydroxypipecolic acid via proline catalyzed alpha-aminooxylation of aldehydes and Pd-catalyzed ether directed aza-Claisen rearrangements

TitleConcise enantioselective synthesis of (2S,3S)-3-hydroxypipecolic acid via proline catalyzed alpha-aminooxylation of aldehydes and Pd-catalyzed ether directed aza-Claisen rearrangements
Publication TypeJournal Article
Year of Publication2015
AuthorsAhuja, BBhushan, Sudalai, A
JournalTetrahedron-Asymmetry
Volume26
Issue1
Pagination24-28
Date PublishedJAN
Type of ArticleArticle
ISSN0957-4166
Abstract

An efficient approach to (2S,3S)-3-hydroxypipecolic acid with an overall yield of 10.2% and 98% ee starting from 1,5-pentanediol has been developed. The key steps employed in the synthesis are the D-proline catalyzed sequential alpha-aminooxylation/Horner-Wadsworth-Emmons olefination of an aldehyde and the Pd-catalyzed MOM-ether directed aza-Claisen rearrangement of an allylic trichloroacetimidate. (C) 2014 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetasy.2014.11.010
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)2.108
Divison category: 
Chemical Engineering & Process Development

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