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Molecules 2010, 15(3), 1291-1301; doi:10.3390/molecules15031291
Article

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

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Received: 14 January 2010 / Revised: 5 February 2010 / Accepted: 2 March 2010 / Published: 4 March 2010
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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 β-ketophosphonates; diastereoselective reduction; γ-amino-β-hydroxy-phosphonates
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Ordóñez, M.; Lagunas-Rivera, S.; Hernández-Núñez, E.; Labastida-Galván, V. Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-Serine. Molecules 2010, 15, 1291-1301.

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