Issue 2, 2012
From the journal:

Organic & Biomolecular Chemistry

Synthesis of geminal bisphosphonates via organocatalyzed enantioselective Michael additions of cyclic ketones and 4-piperidones†

Ana Maria Faísca Phillips*a  and  Maria Teresa Barros*a  

* Corresponding authors

a Department of Chemistry, CQFB-REQUIMTE, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Quinta da Torre, Caparica, Portugal
E-mail: amfp@dq.fct.unl.pt, mtbarros@dq.fct.unl.pt
Fax: +351-212948550
Tel: +351 212948300

Abstract

A Michael addition reaction of cyclic ketones and piperidones to a vinyl phosphonate is described. The reaction, catalyzed by chiral diamines, produced geminal γ-oxobisphosphonates in high yields (up to 92%) and very high ees (up to >99%). Disubstituted ketones gave drs of up to 8 : 92. The synthesis and characterization of several new compounds with potential biological activity is described.

Graphical abstract: Synthesis of geminal bisphosphonates via organocatalyzed enantioselective Michael additions of cyclic ketones and 4-piperidones

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Article information

DOI
https://doi.org/10.1039/C1OB06473H
Article type
Paper
Submitted
28 Aug 2011
Accepted
28 Sep 2011
First published
29 Sep 2011

Org. Biomol. Chem., 2012,10, 404-412

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Synthesis of geminal bisphosphonates via organocatalyzed enantioselective Michael additions of cyclic ketones and 4-piperidones

A. M. Faísca Phillips and M. T. Barros, Org. Biomol. Chem., 2012, 10, 404 DOI: 10.1039/C1OB06473H

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