Intermolecular Pauson-Khand reactions of cyclopropene: a general synthesis of cyclopentanones

I Marchueta; X Verdaguer; A Moyano; M A Pericàs; A Riera

doi:10.1021/ol016505r

Intermolecular Pauson-Khand reactions of cyclopropene: a general synthesis of cyclopentanones

Org Lett. 2001 Oct 4;3(20):3193-6. doi: 10.1021/ol016505r.

Authors

I Marchueta¹, X Verdaguer, A Moyano, M A Pericàs, A Riera

Affiliation

¹ Departament de Química Orgànica, Martí i Franquès, 1-11, Barcelona E-08028, Spain.

PMID: 11574028
DOI: 10.1021/ol016505r

Abstract

[reaction: see text] The Pauson-Khand reaction of cyclopropene with a variety of terminal alkynes has been studied. The best reaction conditions involve NMO activation in CH(2)Cl(2) at -35 degrees C. In this way, 3-substituted-bicyclo[3.1.0]hex-3-en-2-ones have been obtained in good to excellent yields. As a synthetic application, several types of substituted cyclopentenones have been prepared from these cycloadducts by protocols involving conjugate addition and reductive ring opening.