Synthesis of an Inherently Chiral Calix[4]arene Amino Acid and Its Derivatives: Their Application to Asymmetric Reactions as Organocatalysts

The synthesis of an inherently chiral calix[4]arene amino acid as a chiral building block has been achieved in order for subsequent transformation to various types of inherently chiral calix[4]arenes. The optically pure, inherently chiral calix[4]arene amino acids were prepared by the separation of a diastereomeric mixture of calix[4]arene amino acid derivatives bearing a (R)-BINOL moiety. The separated optically pure calix[4]arene amino acid derivatives with a (R)-BINOL moiety were easily transformed to novel inherently chiral calix[4]arenes containing an amino alcohol structure or a quaternary ammonium moiety. These optically pure chiral calix[4]arenes were applied to asymmetric reactions as organocatalysts. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)