RESEARCH ARTICLE

 

The evaluation of novel camphor-derived pyridyl ligands as catalysts in the asymmetric Diels-Alder reaction of cyclopentadiene with 3-acryloyl-2-oxazolidinone

 

 

Grant A. Boyle^I; Thavendran Govender^II; Hendrik G. Kruger^I; Tricia Naicker^I; Glenn E.M. Maguire^I

^ISchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
^IISchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa

 

 

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ABSTRACT

A series of camphor-derived pyridyl ligands were evaluated in the Diels-Alder reaction of 3-acryloyl-2-oxazolidinone 1 with cyclopentadiene 2. High yields with good endo:exo selectivity, but only moderate enantioselectivities (43 % ee), were obtained. The structures of the copper (II) complexes of the ligands were calculated using ONIOM density functional theory and the results suggest that chiral induction to the alkene functional group is indeed lacking. This explains the moderate experimental selectivities obtained.

Keywords: Camphor ligands, asymmetric catalysis, Diels-Alder cycloaddition, computational modelling

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Acknowledgements

This work was supported by grants from the National Research Foundation, GUN 2046819 (South Africa), Aspen Pharmacare and the University of KwaZulu-Natal.

 

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Received 3 March 2009
Revised 25 May 2009
Accepted 28 May 2009

 

 

* To whom correspondence should be addressed. E-mail: kruger@ukzn.ac.za