Organic Letters
Organic Letters
3 years ago

Enantioselective One-Pot Synthesis of α,β-Epoxy Ketones via Aerobic Oxidation of Cyclopropanols

Enantioselective One-Pot Synthesis of α,β-Epoxy Ketones via Aerobic Oxidation of Cyclopropanols
Margus Lopp, Victor Borovkov, Dzmitry G. Kananovich, Gábor Zoltán Elek
An efficient, mild, and environmentally benign method was developed for the asymmetric synthesis of 2-oxyranyl ketones from easily available tertiary cyclopropanols. The one-pot protocol includes the aerobic oxidation of cyclopropanol derivatives catalyzed by Mn(III) complexes followed by the poly-l-leucine-assisted stereoselective elimination of water from the intermediate peroxides with DBU to afford the corresponding epoxy ketones in high yields and good-to-excellent enantioselectivities (up to 97%).

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01519

DOI: 10.1021/acs.orglett.7b01519

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