Organoselenium Accelerated Bromolactonization Reaction.

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.