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 ºC to produce the syn-γ-N-benzylamino-β-hydroxyphosphonates 11 and 13 as a single detectab...

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Main Authors:	Mario Ordóñez, Selene Lagunas-Rivera, Emanuel Hernández-Núñez, Victoria Labastida-Galván
Format:	Article
Language:	English
Published:	MDPI AG 2010-03-01
Series:	Molecules
Subjects:	β-ketophosphonates diastereoselective reduction γ-amino-β-hydroxy-phosphonates
Online Access:	http://www.mdpi.com/1420-3049/15/3/1291/

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spelling	doaj-8725a0a745fb428fbe34d4f8200d20e22020-11-25T02:38:41ZengMDPI AGMolecules1420-30492010-03-011531291130110.3390/molecules15031291Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-SerineMario OrdóñezSelene Lagunas-RiveraEmanuel Hernández-NúñezVictoria Labastida-GalvánThe 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 ºC 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. http://www.mdpi.com/1420-3049/15/3/1291/β-ketophosphonatesdiastereoselective reductionγ-amino-β-hydroxy-phosphonates
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Mario Ordóñez Selene Lagunas-Rivera Emanuel Hernández-Núñez Victoria Labastida-Galván
spellingShingle	Mario Ordóñez Selene Lagunas-Rivera Emanuel Hernández-Núñez Victoria Labastida-Galván Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-Serine Molecules β-ketophosphonates diastereoselective reduction γ-amino-β-hydroxy-phosphonates
author_facet	Mario Ordóñez Selene Lagunas-Rivera Emanuel Hernández-Núñez Victoria Labastida-Galván
author_sort	Mario Ordóñez
title	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_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_sort	synthesis of syn-γ-amino-β-hydroxyphosphonates by reduction of β-ketophosphonates derived from l-proline and l-serine
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2010-03-01
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 ºC 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.
topic	β-ketophosphonates diastereoselective reduction γ-amino-β-hydroxy-phosphonates
url	http://www.mdpi.com/1420-3049/15/3/1291/
work_keys_str_mv	AT marioordonez synthesisofsyngaminobhydroxyphosphonatesbyreductionofbketophosphonatesderivedfromlprolineandlserine AT selenelagunasrivera synthesisofsyngaminobhydroxyphosphonatesbyreductionofbketophosphonatesderivedfromlprolineandlserine AT emanuelhernandeznunez synthesisofsyngaminobhydroxyphosphonatesbyreductionofbketophosphonatesderivedfromlprolineandlserine AT victorialabastidagalvan synthesisofsyngaminobhydroxyphosphonatesbyreductionofbketophosphonatesderivedfromlprolineandlserine
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Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-Serine

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