Issue 24, 2006
From the journal:

Chemical Communications

The o-xylylene protecting group as an element of conformational control of remote stereochemistry in the synthesis of spiroketals†

Patricia Balbuena,a   Enrique M. Rubio,b   Carmen Ortiz Mellet*a  and  José M. García Fernández*b  

* Corresponding authors

a Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado 553, Sevilla, Spain
E-mail: mellet@us.es
Fax: +34 954624960
Tel: +34 954551519

b Instituto de Investigaciones Químicas, CSIC, Américo Vespucio 49, Isla de la Cartuja, Sevilla, Spain
E-mail: jogarcia@iiq.csic.es
Fax: +34-954460565
Tel: +34-954489559

Abstract

Protection of trans-1,2-diol segments as cyclic o-xylylene ethers strongly favours diequatorial over diaxial dispositions; the possibility of using this grouping for remote control of the stereochemistry in the synthesis of spiroketals is here demonstrated by the stereoselective synthesis of tricyclic spirodisaccharides (di-D-fructose dianhydrides).

Graphical abstract: The o-xylylene protecting group as an element of conformational control of remote stereochemistry in the synthesis of spiroketals

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Article information

DOI
https://doi.org/10.1039/B604718A
Article type
Communication
Submitted
31 Mar 2006
Accepted
24 Apr 2006
First published
10 May 2006

Chem. Commun., 2006, 2610-2612

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The o-xylylene protecting group as an element of conformational control of remote stereochemistry in the synthesis of spiroketals

P. Balbuena, E. M. Rubio, C. O. Mellet and J. M. G. Fernández, Chem. Commun., 2006, 2610 DOI: 10.1039/B604718A

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