Shorter and modular synthesis of hemicryptophane-tren derivatives

Org Lett. 2011 Jul 15;13(14):3706-9. doi: 10.1021/ol201355t. Epub 2011 Jun 10.

Abstract

Hemicryptophanes are host molecules with many applications as supramolecular catalysts or in ion selective recognition. A very convenient and efficient modular approach for the synthesis of hemicryptophane-tren (tren, tris(2-aminoethyl)-amine) derivatives has been developed. For instance, hemicryptophane 1 was synthesized at the gram scale in four steps from vanillyl alcohol compared to the previous seven-step procedure. The size, shape, and functionalities of the molecular cavity were also easily modified.