Catalytic formal Homo-Nazarov cyclization

Filippo De Simone; Julien Andrès; Riccardo Torosantucci; Jérôme Waser

doi:10.1021/ol802970g

Catalytic formal Homo-Nazarov cyclization

Org Lett. 2009 Feb 19;11(4):1023-6. doi: 10.1021/ol802970g.

Authors

Filippo De Simone¹, Julien Andrès, Riccardo Torosantucci, Jérôme Waser

Affiliation

¹ Laboratory of Catalysis and Organic Synthesis Ecole Polytechnique Fédérale de Lausanne EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland.

PMID: 19199774
DOI: 10.1021/ol802970g

Abstract

The first catalytic method for the cyclization of vinyl-cyclopropyl ketones (formal homo-Nazarov reaction) is reported. Starting from activated cyclopropanes, heterocyclic, and carbocyclic compounds were obtained under mild conditions using Brønsted acid catalysts. Preliminary investigation of the reaction mechanism indicated a stepwise process.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Combinatorial Chemistry Techniques
Cyclization
Cyclohexanones / chemical synthesis*
Cyclohexanones / chemistry
Cyclopropanes / chemistry*
Ketones / chemistry*
Molecular Structure
Vinyl Compounds / chemistry*

Substances

Cyclohexanones
Cyclopropanes
Ketones
Vinyl Compounds