Synthesis of secondary α-perfluoroalkyl- and tertiary α,α-bis(perfluoroalkyl)-N-methylprolinols and their catalytic activities in the acyl transfer reaction

Various chiral α-perfluoroalkyl-N-methylprolinols were prepared and their organocatalytic activities in an acyl transfer reaction of 4-nitrophenyl 2-methoxyacetate with methanol-d4 in chloroform-d were examined. As a result, α-trifluoromethyl-N-methylprolinol was a more effective acyl transfer catalyst than not only secondary α-perfluorobutyl- and n-butyl-N-methylprolinols but also tertiary α,α-bis(perfluorobutyl)-N-methylprolinol.

Graphical abstractVarious chiral α-perfluoroalkyl-N-methylprolinols were prepared and their organocatalytic activities in an acyl transfer reaction of 4-nitrophenyl 2-methoxyacetate with methanol-d4 in chloroform-d were examined. As a result, α-trifluoromethyl-N-methylprolinol was a more effective acyl transfer catalyst than not only secondary α-perfluorobutyl- and n-butyl-N-methylprolinols but also tertiary α,α-bis(perfluorobutyl)-N-methylprolinol.Figure optionsDownload full-size imageDownload as PowerPoint slide