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

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

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

Fides Benfatti et al. Org Lett. .

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.

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