A Strategy for Synthesizing Axially Chiral Naphthyl-Indoles: Catalytic Asymmetric Addition Reactions of Racemic Substrates
A Strategy for Synthesizing Axially Chiral Naphthyl-Indoles: Catalytic Asymmetric Addition Reactions of Racemic Substrates
复制标题
合成轴向手性萘基吲哚的策略：外消旋底物的催化不对称加成反应
DOI：
10.1002/anie.201908279
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发表时间：
2019-09-10
影响因子：
16.6
通讯作者：
Shi, Feng
中科院分区：
文献类型：
--
作者：
Jiang, Fei;Chen, Ke-Wei;Shi, Feng
通过外消旋萘吲哚与大体积亲电试剂的催化不对称加成反应，建立了轴手性萘吲哚的不对称合成新策略。在手性磷酸催化下，偶氮二甲酸酯和邻羟基苄醇作为大体积的亲电试剂，被C2-未取代的萘基吲哚攻击，进行动态动力学拆分，得到两个系列的轴向手性萘基吲哚，收率高达98%，对映选择性高达98：2 er.
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 a dynamic kinetic resolution to afford two series of axially chiral naphthyl-indoles in good yields (up to 98 %) and high enantioselectivities (up to 98:2 er).