Synthesis of c-alkylcalix[4]arenes. 4. Design, synthesis, and computational studies of novel chiral amido[4]resorcinarenes

摘要

In extending our studies involving BF_3.Et_2O-catalyzed reaction of cinnamic acid analogues, we have shown that amido derivatives also can afford [4]resorcinarene octamethyl ethers. Subse- quently, chiral monomeric amides, derived from the mixed anhydride of cinnamic acid and L- or D-valine, upon treatment with BF_3.Et_2O, yielded for the first time chiral amido [4]resorcinarenes In enantiomerically pure forms. Four stereoisomers were isolated, and three of them were attributed The flattened-cone, chair, and 1,2-alternate conformations.