Department of Pharmacy, Section for Pharmaceutical Chemistry , University of Oslo , P.O. Box 1068, N-0316 Oslo , Norway.
J Org Chem. 2019 Sep 20;84(18):11373-11381. doi: 10.1021/acs.joc.9b01294. Epub 2019 Sep 3.
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.
本文报道了一种高效、区域选择性的溴内酯化反应协议。仅需 0.1 mol%的有机硒化合物（本文中命名为 DECAD），即可在 90 分钟内定量形成具有合成多功能性的溴内酯。DECAD 可从廉价的外消旋樟脑方便地按多克规模制备。所提出的方案易于放大，在克规模上也能同样出色地进行。对反应机理的研究表明，DECAD 原位形成硒翁盐。
