A New Class of Tröger’s Base Analogues Bearing Spiro[4.5] Lactone Straps

Abstract

A protocol for the introduction of spiro[4.5] lactone straps onto the Tröger's base scaffold has been developed. The conversion was found to be most efficient when an appropriate carboxylic acid derivative reacted with 5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocines. Whilst phthaloyl dichloride was the main strap-forming precursor used, other 1,2-unsaturated dicarboxylic acids could be used in the presence of N,N¢-dicyclohexylcarbodiimide.