Fluorinated beta(2)- and beta(3)-Amino Acids: Synthesis and Inhibition of alpha-Chymotrypsin

[摘要]：The synthesis of a series of alpha-fluorinated beta(2)- and beta(3)-amino acid derivatives is described. Stereoselective fluorination at the alpha-carbon of the beta(3)-amino acids was achieved by deprotonation with lithium diisopropylamide followed by treatment with N-fluorobenzenesulfonimide. Fluorination of beta(2)-amino acids employed the chiral auxiliary (4R)-4-benzyl-2-oxazolidinone. The alpha-fluorinated amino acids and their non-fluorinated precursors were found to competitively inhibit alpha-chymotrypsin.

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