Synthetic strategies to alpha-trifluoromethyl and alpha-difluoromethyl substituted alpha-amino acids.
The combination of the unique physical and chemical properties of fluorine with proteinogenic amino acids represents a new approach to the design of biologically active compounds including peptides with improved pharmacological parameters. Therefore, the development of routine synthetic methods which enable the effective and selective introduction of fluorine into the desired amino acids from readily available starting materials is of significant synthetic importance. The scope of this critical review is to summarize the most frequently employed strategies for the synthesis of alpha-difluoromethyl and alpha-trifluoromethyl substituted alpha-amino acids (114 references).
Smits
René
R
Department of Organic Chemistry, FU Berlin, Berlin, Germany. smits@abx.de
Cadicamo
Cosimo Damiano
CD
Burger
Klaus
K
Koksch
Beate
B
D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry
D000596:Amino Acids; D002264:Carboxylic Acids; D005461:Fluorine; D002244:Carbon; D009584:Nitrogen