A novel synthesis of fluorine-containing quaternary amino acid derivatives via palladium-catalyzed allylation reaction

作者：Konno T^*; Kanda M; Ishihara T; Yamanaka H

来源：Journal of Fluorine Chemistry, 2005, 126(11-12): 1517-1523.

DOI：10.1016/j.jfluchem.2005.08.013

• fluorine-containing quaternary amino acids
• allylation
• palladium
• trifluoromethylated leucine analogue

The palladium-catalyzed allylation reaction of trifluoroalanine derivatives with various ally] carbonates was examined. When N-Cbz-protected alanine derivative was employed, the desired C-monoallylated product was obtained in good yield, together with C,N-diallylated and N-monoallylated ones. Changing the protecting group from Cbz to PMP group caused an exclusive formation of C-monoallylated products in high yields. The reaction with various types of allyl carbonates also proceeded smoothly. Based on the present palladium-catalyzed allylation reaction, the total synthesis of alpha-CF3 leucine analogue was achieved.

• 出版日期2005-12