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Microwave-Assisted Tandem Cross Metathesis Intramolecular Aza-Michael Reaction: An Easy Entry to Cyclic β-Amino Carbonyl Derivatives

Santos Fustero,* Diego Jiménez, María Sánchez-Roselló and Carlos del Pozo

*Departamento de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Spain, and Laboratorio de Moléculas Orgánicas, Centro de Investigación Príncipe Felipe, E-46013 Valencia, Spain, Email: santos.fusterouv.es

S. Fustero, D. Jiménez, M. Sánchez-Roselló, C. del Pozo, J. Am. Chem. Soc., 2007, 129, 6700-6701.

DOI: 10.1021/ja0709829 (free Supporting Information)


Abstract

Hoveyda-Grubbs catalyst in combination with BF3·OEt2 efficiently promotes tandem cross metathesis intramolecular aza-Michael reaction between enones and unsaturated carbamates resulting in the creation of β-amino carbonyl units. The use of microwave irradiation dramatically accelerates the process, but also inverts the stereoselectivity in the addition process.

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Key Words

Cross Metathesis, Michael Addition, Pyrrolidines, Piperidines, Microwave Synthesis


ID: J48-Y2007-1710