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Organoselenium Accelerated Bromolactonization Reaction
Jørn E Tungen1, Renate Kristianslund1, Anders Vik1
1Department of Pharmacy, Section for Pharmaceutical Chemistry , University of Oslo , P.O. Box 1068, N-0316 Oslo , Norway.
Abstract:
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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