Journal
ORGANIC LETTERS
Volume 19, Issue 13, Pages 3544-3547Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01519
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Funding
- European Union's Seventh Framework Program for research, technological development and demonstration [621364]
- Centre of Excellence in Molecular Cell Engineering [2014-2020.4.01.15-0013]
- Estonian Ministry of Education and Research [IUT 19-32]
- Tallinn University of Technology (TTU) [B58]
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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%).
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