Organic Chemistry Portal

Abstracts

Search:

Intramolecular PIFA-Mediated Alkyne Amidation and Carboxylation Reaction

Imanol Tellitu,* Sonia Serna, M. Teresa Herrero, Isabel Moreno, Esther Domínguez and Raul SanMartin

*Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain, Email: imanol.tellituehu.es

I. Tellitu, S. Serna, M. T. Herrero, I. Moreno, E. Domínguez, R. SanMartin, J. Org. Chem., 2007, 72, 1526-1529.

DOI: 10.1021/jo062320s (free Supporting Information)


Abstract

The hypervalent iodine reagent PIFA promotes the efficient intramolecular electrophilic cyclization of easily accessible alkynylamides and alkynyl carboxylic acids, leading to pyrrolidinone and lactone skeletons, respectively. A synthetic study and a mechanistic proposal for these transformations are presented.

see article for more examples



Key Words

PIFA, lactones, lactams


ID: J42-Y2007-0650