Synthesis and properties of optically active podands incorporating sulfoxide functionality

Abstract

A series of optically active podands incorporating ether and chiral sulfoxide functionality have been synthesized. The podands formed relatively strong complexes with protonated amines. Where racemic guests were used, the diastereoisomeric complexes were identified in solution by ¹H n.m.r. spectroscopy but the energies of formation of these complexes were too similar to afford optical resolution of guests. The podands influenced the stereochemistry of t-butoxide-catalysed additions of methyl 1-oxoindane-2-carboxylate to methyl vinyl ketone, but stereoselectivities observed were low.