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

Various chiral alpha-perfluoroalkyl-N-methylprolinols were prepared and their organocatalytic activities in an acyl transfer reaction of 4-nitrophenyl 2-methoxyacetate with methanol-d(4) in chloroform-d were examined. As a result, alpha-trifluoromethyl-N-methylprolinol was a more effective acyl transfer catalyst han not only secondary alpha-perfluorobutyl- and n-butyl-N-methylprolinols but also tertiary alpha,alpha-bis(perfluorobutyl)-N-methylprolinol. (C) 2009 Elsevier B.V. All rights reserved.