Er(OTf)3 as a Valuable Catalyst in a Short Synthesis of 2′,3′-Dideoxy Pyranosyl Nucleosides via Ferrier Rearrangement

Antonio Procopio; Renato Dalpozzo; Antonio De Nino; Monica Nardi; Manuela Oliverio; Beatrice Russo

doi:10.1055/s-2006-942443

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Synthesis 2006(15): 2608-2612
DOI: 10.1055/s-2006-942443

PAPER

Er(OTf)₃ as a Valuable Catalyst in a Short Synthesis of 2′,3′-Dideoxy Pyranosyl Nucleosides via Ferrier Rearrangement

Antonio Procopio*^a, Renato Dalpozzo^b, Antonio De Nino^b, Monica Nardi^b, Manuela Oliverio^a, Beatrice Russo^a
^a Dipartimento Farmaco-Biologico, Università degli Studi della Magna Grascia Complesso Ninì Barbieri, Roccelletta di Borgia (CZ) 88021, Italy
Fax: +39(0961)391270; e-Mail: procopio@unicz.it;
^b Dipartimento di Chimica, Università della Calabria, Ponte Bucci, Arcavacata di Rende (CS), 87030, Italy

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Publication History

Received 14 February 2006
Publication Date:
28 June 2006 (online)

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Abstract

Er(OTf)₃ is a useful catalyst for the Ferrier rearrangement furnishing 2′,3′-dideoxy pyranosyl nucleosides easily by means of cleaner reaction profiles, short reaction times, mild reaction conditions, good stereoselectivity, and good recoverability of the commercially available catalyst.

Key words

Ferrier rearrangement - erbium(III) triflate - Lewis acid catalyst - nucleosides - glycals

References

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The purity of recovered Er(OTf)₃ was confirmed by comparison with the IR spectrum of the commercial product.