Synthesis of syn-gamma-amino-beta-hydroxyphosphonates by reduction of beta-ketophosphonates derived from L-proline and L-serine

Mario Ordóñez; Selene Lagunas-Rivera; Emanuel Hernández-Núñez; Victoria Labastida-Galván

doi:10.3390/molecules15031291

Synthesis of syn-gamma-amino-beta-hydroxyphosphonates by reduction of beta-ketophosphonates derived from L-proline and L-serine

Molecules. 2010 Mar 4;15(3):1291-301. doi: 10.3390/molecules15031291.

Authors

Mario Ordóñez¹, Selene Lagunas-Rivera, Emanuel Hernández-Núñez, Victoria Labastida-Galván

Affiliation

¹ Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Mor., México. palacios@ciq.uaem.mx

Abstract

The reduction of gamma-N-benzylamino-beta-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 degrees C to produce the syn-gamma-N-benzylamino-beta-hydroxyphosphonates 11 and 13 as a single detectable diastereoisomer, under non-chelation or Felkin-Anh model control.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Magnetic Resonance Spectroscopy
Mass Spectrometry
Organophosphonates / chemical synthesis*
Oxidation-Reduction
Proline / chemistry*
Serine / chemistry*
Stereoisomerism

Substances

Organophosphonates
Serine
Proline