Herein, we demonstrate that organic, single-electron oxidant in the presence of diarylprolinol silylether type catalyst serves as a tool for the transformation of electron-rich enamines to iminium ions. These iminium ions take part in a subsequent Michael-initiated ring-closure (MIRC) reaction with in situ present nucleophile giving rise to overall cyclopropanation reaction of saturated aldehydes. Stereodefined cyclopropanes are obtained in high yields and selectivities. This one-pot transformation represents the additional example of saturated aldehydes being used in the coupled one-pot processes. (Figure presented.).
CITATION STYLE
Džambaski, Z., Bondžić, A. M., Triandafillidi, I., Kokotos, C. G., & Bondžić, B. P. (2021). Organocatalytic, Organic Oxidant Promoted, Enamine C−H Oxidation/Cyclopropanation Reaction. Advanced Synthesis and Catalysis, 363(16), 4002–4008. https://doi.org/10.1002/adsc.202100630
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