Scharinger, F., Pálvölgyi, Á. M., Weisz, M., Weil, M., Stanetty, C., Schnürch, M., & Bica-Schröder, K. (2022). Sterically Demanding Flexible Phosphoric Acids for Constructing Efficient and Multi-Purpose Asymmetric Organocatalysts. Angewandte Chemie International Edition, 61(26), Article e202202189. https://doi.org/10.1002/anie.202202189
Herein, we present a novel approach for various asymmetric transformations of cyclic enones. The combination of readily accessible chiral diamines and sterically demanding flexible phosphoric acids resulted in a simple and highly tunable catalyst framework. The careful optimization of the catalyst components led to the identification of a particularly powerful and multi-purpose organocatalyst, which was successfully applied for asymmetric epoxidations, aziridinations, aza-Michael-initiated cyclizations, as well as for a novel Robinson-like Michael-initiated ring closure/aldol cyclization. High catalytic activities and excellent stereocontrol was observed for all four reaction types, indicating the excellent versatility of our catalytic system. Furthermore, a simple change in the diamine's configuration provided easy access to both product antipodes in all cases.
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Forschungsinfrastruktur:
Analytical Instrumentation Center
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Projekttitel:
Kontinourliche Umsetzung von CO2 in ionischen Flüssigkeiten: 7465546 - 04/12/2019 (European Commission) Ionenaggregation von chiralen ionischen Flüssigkeiten: P 29146 (Fonds zur Förderung der wissenschaftlichen Forschung (FWF))