Department of Chemistry , Indian Institute of Technology Ropar , Nangal Road , Rupnagar , Punjab 140001 , India.
Org Lett. 2018 Sep 7;20(17):5163-5166. doi: 10.1021/acs.orglett.8b02094. Epub 2018 Aug 15.
A single-step TiX-mediated Prins-type cyclization of cyclopropane carbaldehydes with 3-buten-1-ol for the highly stereoselective construction of relatively strained ( E)-hexahydrooxonines is reported. Switching the alcohol to 3-butyn-1-ol prompted a similar route, augmented by another cyclization within a nine-membered ring to afford a bicyclized product (4,4-dihalo-5-aryloctahydrocyclopenta[ b]pyran). Easy transformation of the resulting geminal dihalide to a vinyl halide and a ketone further supplemented the substance of this approach.
报道了一种通过 TiX 介导的丙醛环丙烷与 3-丁烯-1-醇的一步 Prins 型环化反应，用于高度立体选择性地构建相对紧张的(E)-六氢氧杂氮酮。将醇切换为 3-丁炔-1-醇会引发类似的途径，通过在九元环内进行另一次环化反应，得到双环化产物（4,4-二卤代-5-芳基八氢环戊并[b]吡喃）。通过容易将得到的偕二卤化物转化为卤代乙烯和酮，进一步补充了这种方法的内容。
