Syntheses of chiral β-amino α-perfluoroalkylpropanol derivatives

Chiral β-amino α-perfluoroalkylpropanol derivatives were synthesized from N-Boc-l-phenylalanine methyl ester by substitution of the methoxy group into the corresponding perfluoroalkyl chain, followed by reduction and deprotection. Among them, a Schiff base prepared by condensation of (2S,3S)-2-amino-3-perfluorooctyl-1-phenylpropan-3-ol, (2S,3S)-1, and 1-naphthaldehyde catalyzed the asymmetric ethyl addition reaction of diethylzinc with the aldehyde to afford the product up to 93% ee.