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Keywords = γ-amino-β-hydroxy-phosphonates

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11 pages, 387 KiB  
Article
Synthesis of syn-γ-Amino-β-hydroxyphosphonates by Reduction of β-Ketophosphonates Derived from L-Proline and L-Serine
by Mario Ordóñez, Selene Lagunas-Rivera, Emanuel Hernández-Núñez and Victoria Labastida-Galván
Molecules 2010, 15(3), 1291-1301; https://doi.org/10.3390/molecules15031291 - 4 Mar 2010
Cited by 3 | Viewed by 9382
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 [...] Read more.
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. Full article
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