Synthesis of monoacylated derivatives of 1,2- cyclohexanediamine. Evaluation of their catalytic activity in the preparation of Wieland-Miescher ketone

Ángel L Fuentes de Arriba; David G Seisdedos; Luis Simón; Victoria Alcázar; César Raposo; Joaquín R Morán

doi:10.1021/jo101723v

Synthesis of monoacylated derivatives of 1,2- cyclohexanediamine. Evaluation of their catalytic activity in the preparation of Wieland-Miescher ketone

J Org Chem. 2010 Dec 3;75(23):8303-6. doi: 10.1021/jo101723v. Epub 2010 Nov 8.

Authors

Ángel L Fuentes de Arriba¹, David G Seisdedos, Luis Simón, Victoria Alcázar, César Raposo, Joaquín R Morán

Affiliation

¹ Organic Chemistry Department, Plaza de los Caídos 1-5, Universidad de Salamanca, Salamanca 37008, Spain.

PMID: 21058658
DOI: 10.1021/jo101723v

Abstract

Ureas, carbamoyl derivatives, amides, and sulfonamides can be easily prepared from the strained (R,R)-cylohexanediamine urea (1) in high yield, leaving a free amino group that shows good catalytic activity in intramolecular aldol condensations. The preparation of Wieland-Miescher ketone has been studied with these catalysts.