Synthesis and stereochemical analysis of dynamic planar chiral oxa[7]orthocyclophene.

Abstract

Planar chiral C6-substituted oxa[7]orthocyclophenes were designed and synthesized, and their stereochemical behavior was analyzed. The Kumada-Tamao coupling of the C6-iodo-substituted oxacyclophene enabled the efficient and divergent synthesis of C6-substituted derivatives. The stereochemical analysis of the oxacyclophenes revealed that the iodo- and methyl-substituted derivatives have reasonable stereochemical stability. The planar chirality of the methyl-substituted oxacyclophene was successfully transformed into central chirality by epoxidation without loss of enantiomeric purity.