Iron-Catalyzed [3 + 2] Annulation of Aminocyclopropanes with Aldehydes: Stereoselective Synthesis of Aminotetrahydrofurans

Iron-Catalyzed [3 + 2] Annulation of Aminocyclopropanes with Aldehydes: Stereoselective Synthesis of Aminotetrahydrofurans

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...

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Veröffentlicht in:Organic letters 2012-01, Vol.14 (1), p.386-389
Hauptverfasser: Benfatti, Fides, Nanteuil, Florian de, Waser, Jérôme
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol203144v