929031-14-1Relevant articles and documents
Asymmetric synthesis of deuterated and fluorinated aromatic α,α-disubstituted amino acid derivatives
Hartmann, Caroline E.,Baumann, Thomas,Baechle, Michael,Braese, Stefan
scheme or table, p. 1341 - 1349 (2010/10/21)
We herein present organocatalytic approaches to synthesize fluorinated and deuterated α-substituted phenylglycine derivatives. Whereas the addition of diethyl azodicarboxylate to fluorinated α-substituted aldehydes furnishes chiral non-racemic compounds, the use of chloramine-T as a nitrogen source represents a rapid access to sulfamidated fluorinated amino acid precursors. Additionally, further functionalization was achieved through the palladium-catalyzed coupling of a p-bromosubstituted aldehyde with a range of fluorine or deuterium-containing boronic acids. Oxidation of the aldehyde function and cleavage of the protection group of the nitrogen give way to the free fluorinated unnatural amino acids.
