Issue 16, 2010
From the journal:

Organic & Biomolecular Chemistry

Experimental and computational study of the ring opening of tricyclic oxanorbornenes to polyhydro isoindole phosphonates†‡

Diederica D. Claeys,ab   Christian V. Stevens,*a   Bart I. Roman,a   Pieter Van De Caveye,a   Michel Waroquierb  and  Veronique Van Speybroeck*b  

* Corresponding authors

a Research group SynBioC, Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, Ghent, Belgium
E-mail: Chris.Stevens@UGent.be
Fax: +32 9 264 6243
Tel: +32 9 264 5950

b Center for Molecular Modeling, Ghent University, Technologiepark 903, QCMM – alliance, Ghent-Brussels, Belgium, Belgium
E-mail: Veronique.VanSpeybroeck@UGent.be
Tel: +32 9 264 6558

Abstract

Phosphonylated azaheterocycles are an important class of compounds with high biological potential as conformationally restricted bioisosteres of amino acids. Therefore, it is of interest to synthesize conformationally constrained amino phosphonates. We wanted to investigate possible routes via ring opening of α-amino phosphonates with an oxanorbornene skeleton, as these can be synthesized with high stereoselectivity. This was achieved using different Lewis acids, leading to a range of products. The reaction with TiCl4 and FeCl3 was modelled at a DFT level of theory to get insight in the pathways towards the corresponding products. To ease the work up, the Fe(III) catalyst was coated on montmorillonite clay, but this accelerated aromatization after ring opening. Quenching the FeCl3 catalyzed reaction mixture on celite caused complete aromatization.

Graphical abstract: Experimental and computational study of the ring opening of tricyclic oxanorbornenes to polyhydro isoindole phosphonates

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Article information

DOI
https://doi.org/10.1039/C002926B
Article type
Paper
Submitted
15 Feb 2010
Accepted
14 May 2010
First published
11 Jun 2010

Org. Biomol. Chem., 2010,8, 3644-3654

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Experimental and computational study of the ring opening of tricyclic oxanorbornenes to polyhydro isoindole phosphonates

D. D. Claeys, C. V. Stevens, B. I. Roman, P. Van De Caveye, M. Waroquier and V. Van Speybroeck, Org. Biomol. Chem., 2010, 8, 3644 DOI: 10.1039/C002926B

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