Journal
ORGANIC LETTERS
Volume 17, Issue 4, Pages 904-907Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b00018
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Funding
- National Basic Research Program of China [2009CB623505]
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An in situ formed porphyrin-inspired iron complex that catalyzes asymmetric epoxidation of di- and trisubstituted enones is described. The reaction provides highly enantioenriched alpha,beta-epoxyketones (up to 99% ee). The practical utility of the new catalyst system is demonstrated by the gram-scale synthesis of optically pure epoxide. Hammett analysis suggests that the transition state of the reaction is electron-demanding and the active oxidant is electrophilic.
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