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Issue 2, 2009

Synthesis and analytical resolution of chiral pyrazoles derived from (5R)-dihydrocarvone

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Abstract

In the course of the development of chiral hydrotris(pyrazolyl)borate ligands for unidirectional molecular machines, we have investigated the preparation of original chiral pyrazoles using (5R)-dihydrocarvone as starting material. Of the two synthetic routes examined and described in this article, the most efficient one involved the formation of the pyrazole ring in a last step. This method appeared very efficient and granted access to a pyrazole functionalized with an ester group for subsequent deposition of the corresponding tris(pyrazolyl)borate on insulating oxide surfaces. Analytical HPLC confirmed the presence of a mixture of four diastereoisomers.

Graphical abstract: Synthesis and analytical resolution of chiral pyrazoles derived from (5R)-dihydrocarvone

Article information


Submitted
15 Jul 2008
Accepted
21 Aug 2008
First published
24 Oct 2008

New J. Chem., 2009,33, 293-299
Article type
Paper

Synthesis and analytical resolution of chiral pyrazoles derived from (5R)-dihydrocarvone

H. J. de Rouville, G. Vives, E. Tur, J. Crassous and G. Rapenne, New J. Chem., 2009, 33, 293 DOI: 10.1039/B812123K

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