Synthesis and Applications of (-)-(S)-3-Aminoquinuclidine- Derived Thiourea
2015
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.


Keywords
aminoquinuclidine, bifunctional thiourea organocatalysts, asymmetric synthesis, Chiralpak IA.
DOI
10.7250/msac.2015.002

Rolava, E., Turks, M. Synthesis and Applications of (-)-(S)-3-Aminoquinuclidine- Derived Thiourea. Materials Sciences and Applied Chemistry. Vol.31, 2015, pp.10-15. ISSN 1407-7353. e-ISSN 2255-8713. Available from: doi:10.7250/msac.2015.002

Publication language
English (en)
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