Journal
ORGANIC LETTERS
Volume 21, Issue 24, Pages 10094-10098Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04072
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Funding
- Austrian COMET Program by the Austrian Federal Ministry of Transport, Innovation and Technology (BMVIT) [862766]
- Austrian COMET Program by the Austrian Federal Ministry of Science, Research and Economy (BMWFW) [862766]
- Austrian COMET Program by the State of Styria (Styrian Funding Agency SFG) [862766]
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A scalable procedure for the direct preparation of epoxides from ketones has been developed. The method is based on the carefully controlled generation of (bromomethyl)lithium (LiCH2Br) from inexpensive CH2Br2 and MeLi in a continuous flow reactor. The reaction has shown excellent selectivity for a variety of substrates, including a-chloroketones, which typically fail under classic Corey Chaykovsky conditions. This advantage has been used to develop a novel route toward the drug fluconazole.
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