A Strategy for Synthesizing Axially Chiral Naphthyl‐Indoles: Catalytic Asymmetric Addition Reactions of Racemic Substrates
作者:Fei Jiang、Ke‐Wei Chen、Ping Wu、Yu‐Chen Zhang、Yinchun Jiao、Feng Shi
DOI:10.1002/anie.201908279
日期:2019.10.14
A new strategy for enantioselective synthesis of axially chiral naphthyl-indoles has been established through catalytic asymmetric addition reactions of racemic naphthyl-indoles with bulky electrophiles. Under chiral phosphoric acid catalysis, azodicarboxylates and o-hydroxybenzyl alcohols served as bulky but reactive electrophiles that were attacked by C2-unsubstituted naphthyl-indoles, which underwent
通过外消旋萘基吲哚与大体积亲电试剂的催化不对称加成反应,建立了轴向手性萘基吲哚对映选择性合成的新策略。在手性磷酸催化下,偶氮二羧酸盐和邻羟基苄醇用作笨重但反应性的亲电试剂,它们被C2-未取代的萘吲哚攻击,后者经历了动态动力学拆分,从而以良好的收率得到了两个系列的轴向手性萘基吲哚。至98%)和高对映选择性(高达98:2 er)。