A new synthetic strategy to prepare throne and calix diastereoisomers of parallel tris-Tröger's bases

Abstract

The calix diastereoisomers of the parallel tris-Tröger's base (tris-TB) derivatives were suggested as potential cavitands in 2002, and the first members of this cavitand family were introduced in 2007. The synthetic strategy enabling the preparation of naphthalene and anthracene derivatives of parallel tris-TBs, i.e. preparation without any reduction step, is introduced. Naphthalene calix-tris-TB derivative having a cavity volume of about 0.113 nm³ (65% of α-CD cavity) is prepared by isomerisation in various acid conditions.

Keywords:

• parallel tris-Tröger's base
• diastereoisomerisation
• cavitand

Acknowledgement

This work was supported by the Grant Agency of the Czech Republic (P207/11/P121).