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

doi:10.3390/molecules15031291

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

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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.

Received: 14 January 2010; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

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(3):1291-1301.

Chicago/Turabian Style

Ordóñez, Mario; Lagunas-Rivera, Selene; Hernández-Núñez, Emanuel; Labastida-Galván, Victoria. 2010. "Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-Serine." Molecules 15, no. 3: 1291-1301.

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