Enantioselective Cascade Formal Reductive Insertion of Allylic Alcohols into the C(O)–C Bond of 1,3-Diketones: Ready Access to Synthetically Valuable 3-Alkylpentanol Units
作者:Mylène Roudier、Thierry Constantieux、Adrien Quintard、Jean Rodriguez
DOI:10.1021/ol500821c
日期:2014.6.6
An unprecedented cascade reaction combining dual iron–amine-catalyzed enantioselective functionalization of allylic alcohols and chemoselective acyl transfer is presented. It allows, from diketones and allylic alcohols, preparation of efficiently functionalized γ-chiral alcohols in up to 96% yield and 96:4 er. The interest of this redox-, atom-, and step-economomical approach was further demonstrated
提出了空前的级联反应,结合了铁-胺催化的烯丙醇对映选择性官能化和化学选择性酰基转移。它可以从二酮和烯丙基醇制备高效官能化的γ-手性醇,收率高达96%和96:4 er。这种氧化还原,原子和步经济学方法的兴趣在生物活性天然产物或加味剂分子的几个关键片段的短合成中得到了进一步证明。