Iron-catalyzed [3 + 2] annulation of aminocyclopropanes with aldehydes: stereoselective synthesis of aminotetrahydrofurans

Fides Benfatti; Florian de Nanteuil; Jérôme Waser

doi:10.1021/ol203144v

Iron-catalyzed [3 + 2] annulation of aminocyclopropanes with aldehydes: stereoselective synthesis of aminotetrahydrofurans

Org Lett. 2012 Jan 6;14(1):386-9. doi: 10.1021/ol203144v. Epub 2011 Dec 21.

Authors

Fides Benfatti¹, Florian de Nanteuil, 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: 22188445
DOI: 10.1021/ol203144v

Abstract

The first method for the [3 + 2] annulation of donor-acceptor aminocyclopropanes with aldehydes is reported. The reaction is catalyzed by iron trichloride on alumina in yields up to 99% and with excellent cis selectivities (up to >20:1) and represents a stereoselective and atom economic access to valuable 2-aminotetrahydrofurans, which constitute the core of DNA and RNA.