Divergent syntheses of both ring-open cyclopropanes and tetrahydroquinolinones were achieved using Sc(OTf)3 as the catalyst. When 3 mol% of Sc(OTf)3 was used in CH3CN, enaminone addition to cyclopropane occurred resulting in ring-opening products. Increasing the catalyst loading to 30 mol%, tetrahydroquinolinones were formed via a new dehydrogenative Csp2-C sp3 cross-coupling reaction. The yields for both reactions were good to excellent. The mechanism of the dehydrogenative Csp2-C sp3 cross-coupling reaction was investigated. This is the first example of using α-enaminone with donor-acceptor cyclopropanes for both methods. Current stereospecific and asymmetric reactions conditions are present as well.

Divergent synthesis of tetrahydroquinolinones and ring-open cyclopropanes using α-enaminone with donor-acceptor cyclopropanes

ACS Spring 2022

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