synthesis of syn-γ-amino-β-hydroxyphosphonates by reduction of β-ketophosphonates derived from l-proline and l-serine合成的syn-γ-amino-β-hydroxyphosphonates减少β-ketophosphonates源自l-proline l-serine.pdf

Molecules 2010, 15, 1291-1301; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-Serine Mario Ordóñez *, Selene Lagunas-Rivera, Emanuel Hernández-Núñez and Victoria Labastida-Galván Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209 Cuernavaca, Mor., México ∗ Author to whom correspondence should be addressed; E-Mail: palacios@ciq.uaem.mx; Tel.: +527773297997; Fax: +527773297997. Received: 14 January 2010; in revised form: 5 February 2010 / Accepted: 2 March 2010 / Published: 4 March 2010 Abstract: 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. Keywords: β-ketophosphonates; diastereoselective reduction; γ-amino-β-hydroxy- phosphonates 1. Introduction Aminoalkylphosphonic acids are structurally analogous to the amino acids, obtained by isosteric substitution of the planar and less bulky carboxylic acid (CO H) group by a tetrahedral phosphonic a