Synthesis and Applications of (-)-(S)-3-Aminoquinuclidine- Derived Thiourea

Evija Rolava, Māris Turks


A synthesis of enantiopure thiourea organocatalyst based on (-)-(S)-3-aminoquinuclidine dihydrochloride was developed with quantitative product yield. The catalyst was tested in different reactions: asymmetric Michael addition of ketones and malonates to nitroalkenes, nitromethane 1,4-addition to trans-chalcone, and Friedel-Crafts alkylation of indoles with trans-β-nitrostyrene. The novel thiourea proved to catalyze the aforementioned reactions and expected products were obtained in mediocre yields and low enantioselectivities.


aminoquinuclidine, bifunctional thiourea organocatalysts, asymmetric synthesis, Chiralpak IA.

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DOI: 10.7250/msac.2015.002