Issue 33, 2010
From the journal:

Chemical Communications

Formation and reactivity of new Nicholas–Ferrier pyranosidic cations: novel access to oxepanes via a 1,6-hydride shift/cyclization sequence†

Ana M. Gómez,*a   Fernando Lobo,a   Daniel Pérez de las Vacas,a   Serafín Valverdea  and  J. Cristóbal López*a  

* Corresponding authors

a Instituto de Química Orgánica General (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain
E-mail: anagomez@iqog.csic.es, clopez@iqog.csic.es

Abstract

Pyranosidic allylic (Ferrier) cations that share dicobalt hexacarbonyl propargyl (Nicholas) stabilization at C-1 display a remarkable reactivity leading to either substituted oxepanes or 3-C-branched pyranosides, depending on the substituent at O-6.

Graphical abstract: Formation and reactivity of new Nicholas–Ferrier pyranosidic cations: novel access to oxepanes via a 1,6-hydride shift/cyclization sequence

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Article information

DOI
https://doi.org/10.1039/C0CC00586J
Article type
Communication
Submitted
25 Mar 2010
Accepted
25 Jun 2010
First published
26 Jul 2010

Chem. Commun., 2010,46, 6159-6161

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Formation and reactivity of new Nicholas–Ferrier pyranosidic cations: novel access to oxepanes via a 1,6-hydride shift/cyclization sequence

A. M. Gómez, F. Lobo, D. Pérez de las Vacas, S. Valverde and J. C. López, Chem. Commun., 2010, 46, 6159 DOI: 10.1039/C0CC00586J

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