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; in revised form: 5 February 2010 / Accepted: 2 March 2010 / Published: 4 March 2010
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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