Literature DB >> 15606105

Diastereoselective synthesis of (2S,5R)-5-hydroxypipecolic acid and 6-substituted derivatives.

Peter N M Botman1, F Jan Dommerholt, René de Gelder, Quirinus B Broxterman, Hans E Schoemaker, Floris P J T Rutjes, Richard H Blaauw.   

Abstract

[reaction: see text] Herein, we report a diastereoselective synthesis of the natural product (2S,5R)-5-hydroxypipecolic acid and 6-substituted derivatives thereof. The key step in the synthetic sequence is a novel highly diastereoselective epoxidation reaction of an enantiomerically pure cyclic enamide intermediate.

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Year:  2004        PMID: 15606105     DOI: 10.1021/ol047774v

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  Alternative Reactivity of Leucine 5-Hydroxylase Using an Olefin-Containing Substrate to Construct a Substituted Piperidine Ring.

Authors:  Lide Cha; Sergey Milikisiyants; Madison Davidson; Shan Xue; Tatyana Smirnova; Alex Smirnov; Yisong Guo; Wei-Chen Chang
Journal:  Biochemistry       Date:  2020-05-18       Impact factor: 3.162

Review 2.  Chiral secondary amino acids, their importance, and methods of analysis.

Authors:  Helena Zahradníčková; Stanislav Opekar; Lucie Řimnáčová; Petr Šimek; Martin Moos
Journal:  Amino Acids       Date:  2022-02-21       Impact factor: 3.520

3.  Concise and straightforward asymmetric synthesis of a cyclic natural hydroxy-amino acid.

Authors:  Mario J Simirgiotis; Javier Vallejos; Carlos Areche; Beatriz Sepúlveda
Journal:  Molecules       Date:  2014-11-26       Impact factor: 4.411

4.  Characterization of Cyclic N-Acyliminium Ions by Infrared Ion Spectroscopy.

Authors:  Jona Merx; Kas J Houthuijs; Hidde Elferink; Eva Witlox; Jasmin Mecinović; Jos Oomens; Jonathan Martens; Thomas J Boltje; Floris P J T Rutjes
Journal:  Chemistry       Date:  2021-12-29       Impact factor: 5.020

  4 in total

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