182998-49-8Relevant academic research and scientific papers
Enantiomerically pure α-fluoroalkyl-α-amino acids: Synthesis of (R)-α-difluoromethyl-alanine and (S)-α-difluoromethyl-serine
Bravo, Pierfrancesco,Capelli, Silvia,Meille, Stefano V.,Seresini, Paolo,Volonterio, Alessandro,Zanda, Matteo
, p. 2321 - 2332 (2007/10/03)
Hydrocyanation of enantiomerically pure N-Cbz α-fluoroalkyl β-sulfinylenamines 1 occurs smoothly by treatment with KCN or by addition of trimethylsilylcyanide or diethyl phosphorocyanidate to preformed sodium derivatives of 1. The diastereoisomeric difluoro α-aminonitriles 2b have been transformed in the unnatural amino acids (R)-α-difluoromethyl-alanine and (S)-α-difluoromethyl-serine.
A new strategy for the synthesis of α-difluoromethyl-substituted α-hydroxy and α-amino acids
Osipov, Sergey N.,Golubev, Alexander S.,Sewald, Norbert,Michel, Thomas,Kolomiets, Alexey F.,Fokin, Alexander V.,Burger, Klaus
, p. 7521 - 7528 (2007/10/03)
A new method for the preparation of α-chlorodifluoromethyl-, α-bromodifluoromethyl-, and α-difluoromethyl-substituted α-hydroxy and α-amino acid esters 11, 19-21 is described. The key step of the synthesis is the regioselective alkylation of ketones 5, 7-9 and imines 16-18 with C-nucleophiles. The ketones 7-9 are readily available from 3,3,3-trifluorolactate 1 by a five-step procedure. Subsequent removal of the protecting groups from 19-21 provides the corresponding free amino acids 25, 26, 28.
