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South African Journal of Chemistry
versión On-line ISSN 1996-840X
versión impresa ISSN 0379-4350
S.Afr.j.chem. (Online) vol.65 Durban 2012
RESEARCH ARTICLE
Comparison of tetrahydroisoquinoline (TIQ) thiazole and oxazoline ligands for asymmetric Henry reactions
Sunayna S. PawarI; Sai Kumar ChakkaII; Pher G. AnderssonII, III; Hendrik G. KrugerII; Glenn E.M. MaguireII; Thavendran GovenderI, *
ISchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Westville Campus, Durban, 4000, South Africa
IISchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Durban, 4000, South Africa
IIIDepartment of Biochemistry and Organic Chemistry, Uppsala University, SE-751 23, Uppsala, Sweden
ABSTRACT
A series of novel C1 symmetric thiazole ligands with a tetrahydroisoquinoline (TIQ) backbone were synthesized. Their application in the catalytic asymmetric Henry reaction was investigated with comparison to a corresponding TIQ oxazoline ligand. The Cu(II)-oxazoline complex was more reactive and furnished moderate enantioselectivities up to 61:36 (syn:anti) with 75:25 diastereomeric excess, while the Cu(II)-thiazole complexes had lower selectivity. This is the first example where a direct comparison between an N, N-type thiazole and oxazoline ligands has been studied.
Keywords: Tetrahydroisoquinoline, thiazole, oxazoline, Henry reaction, enantioselectivity
Full text available only in PDF format.
Acknowledgements
This work was supported by the National Research Foundation (South Africa, GUN 2073251, GUN 58505), SA/Swedish Research Links Programme grant and Aspen Pharmacare, SA.
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Received 21 October 2011
Revised 29 November 2011
Accepted 18 January 2012
Submitted by invitation to celebrate 2011 the 'International Year of Chemistry'.
* To whom correspondence should be addressed. E-mail: govenderthav@ukzn.ac.za