Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-Serine

The reduction of γ-N-benzylamino-β-ketophosphonates 6 and 10, readily available from L-proline and L-serine, respectively, can be carried out in high diastereoselectivity with catecholborane (CB) in THF at -78 °C to produce the syn-γ-N-benzylamino-β-hydroxyphosphonates 11 and 13 as a single detectab...

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Detalles Bibliográficos
Autores principales: Ordóñez, Mario, Lagunas-Rivera, Selene, Hernández-Núñez, Emanuel, Labastida-Galván, Victoria
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257292/
https://www.ncbi.nlm.nih.gov/pubmed/20335981
http://dx.doi.org/10.3390/molecules15031291
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author Ordóñez, Mario
Lagunas-Rivera, Selene
Hernández-Núñez, Emanuel
Labastida-Galván, Victoria
author_facet Ordóñez, Mario
Lagunas-Rivera, Selene
Hernández-Núñez, Emanuel
Labastida-Galván, Victoria
author_sort Ordóñez, Mario
collection PubMed
description The reduction of γ-N-benzylamino-β-ketophosphonates 6 and 10, readily available from L-proline and L-serine, respectively, can be carried out in high diastereoselectivity with catecholborane (CB) in THF at -78 °C to produce the syn-γ-N-benzylamino-β-hydroxyphosphonates 11 and 13 as a single detectable diastereoisomer, under non-chelation or Felkin-Anh model control.
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spelling pubmed-62572922018-12-04 Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-Serine Ordóñez, Mario Lagunas-Rivera, Selene Hernández-Núñez, Emanuel Labastida-Galván, Victoria Molecules Article The reduction of γ-N-benzylamino-β-ketophosphonates 6 and 10, readily available from L-proline and L-serine, respectively, can be carried out in high diastereoselectivity with catecholborane (CB) in THF at -78 °C to produce the syn-γ-N-benzylamino-β-hydroxyphosphonates 11 and 13 as a single detectable diastereoisomer, under non-chelation or Felkin-Anh model control. Molecular Diversity Preservation International 2010-03-04 /pmc/articles/PMC6257292/ /pubmed/20335981 http://dx.doi.org/10.3390/molecules15031291 Text en © 2010 by the authors; http://creativecommons.org/licenses/by/3.0/ licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Ordóñez, Mario
Lagunas-Rivera, Selene
Hernández-Núñez, Emanuel
Labastida-Galván, Victoria
Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-Serine
title Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-Serine
title_full Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-Serine
title_fullStr Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-Serine
title_full_unstemmed Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-Serine
title_short Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-Serine
title_sort synthesis of syn-γ-amino-β-hydroxyphosphonates by reduction of β-ketophosphonates derived from l-proline and l-serine
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257292/
https://www.ncbi.nlm.nih.gov/pubmed/20335981
http://dx.doi.org/10.3390/molecules15031291
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