Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 18, Pages 11373-11381Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01294
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Funding
- Research Council of Norway [FRIPRO-FRINATEK 230470]
- Department of Pharmacy, University of Oslo
- Norwegian Ph.D. School in Pharmacy (Nasjonal forskerskole i farmasi, NFIF)
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A highly efficient and regioselective bromolactonization protocol is reported. The quantitative formation of synthetically versatile bromolactones occurs in the presence of only 0.1 mol % of an organoselenium compound, coined DECAD herein, within 90 min. DECAD is conveniently prepared on multigram scale from cheap racemic camphor. The presented protocol was easy to scale up and performed equally well on gram scale. Investigation of the mechanism revealed that DECAD forms a selenonium ylene in situ.
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