Enantioselective recognition of 1,2-aminoalcohols by the binol receptor dangled with pyrrole-2-carboxamide and its analogues

Abstract

Novel binol receptor with pyrrole-2-carboxamide moiety and its analogues have been designed, synthesized, and used to enantioselectively recognize 1,2-aminoalcohols via multiple hydrogen bonding. The pyrrole-based binol receptor showed the highest enantioselectivity among the four receptors as determined by the 1H NMR. The DFT calculation strongly supports complementary hydrogen bonding between alcoholic -OH and pyrrolyl groups. © 2008 Elsevier Ltd. All rights reserved.