Naicker T., Arvidsson P.I., Kruger H.G., Maguire G.E.M., Govender T.
School of Pharmacy and Pharmacology, University of KwaZulu-Natal, Private Bag 4000, Durban, South Africa; Department of Medicinal Chemistry, Uppsala Biomedical Centre, Uppsala University, 75123 Uppsala, Sweden; Innovative Medicines, CNSP IMed, AstraZeneca RandD Sodertalje, 15185 Sodertalje, Sweden; School of Chemistry, University of KwaZulu-Natal, Westville, Durban, South Africa
Naicker, T., School of Pharmacy and Pharmacology, University of KwaZulu-Natal, Private Bag 4000, Durban, South Africa; Arvidsson, P.I., School of Pharmacy and Pharmacology, University of KwaZulu-Natal, Private Bag 4000, Durban, South Africa, Department of Medicinal Chemistry, Uppsala Biomedical Centre, Uppsala University, 75123 Uppsala, Sweden, Innovative Medicines, CNSP IMed, AstraZeneca RandD Sodertalje, 15185 Sodertalje, Sweden; Kruger, H.G., School of Chemistry, University of KwaZulu-Natal, Westville, Durban, South Africa; Maguire, G.E.M., School of Chemistry, University of KwaZulu-Natal, Westville, Durban, South Africa; Govender, T., School of Pharmacy and Pharmacology, University of KwaZulu-Natal, Private Bag 4000, Durban, South Africa
The simple and practical syntheses of chiral guanidine organocatalysts and their evaluation in the asymmetric Michael addition reaction of malonates and β-keto esters with nitro-olefins is reported. These organocatalysts are the first of their kind based on a tetrahydroisoquinoline framework. In addition, a microwave-assisted procedure for introducing the guanidine unit onto amino amide derivatives is reported. The chiral products were obtained with quantitative chemical efficiency (up to 99 % yield) and excellent enantioselectivity (up to 97 % ee). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.