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轴向手性萘基-吲哚骨架的设计与对映选择性构建。

Design and Enantioselective Construction of Axially Chiral Naphthyl-Indole Skeletons.

机构信息

School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, P.R. China.

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P.R. China.

出版信息

Angew Chem Int Ed Engl. 2017 Jan 2;56(1):116-121. doi: 10.1002/anie.201608150. Epub 2016 Nov 3.

DOI:10.1002/anie.201608150
PMID:27809384
Abstract

The first enantioselective construction of a new class of axially chiral naphthyl-indole skeletons has been established by organocatalytic asymmetric coupling reactions of 2-naphthols with 2-indolylmethanols (up to 99 % yield, 97:3 e.r.). This approach not only affords a new type of axially chiral heterobiaryl backbone, but also provides a new catalytic enantioselective strategy for constructing axially chiral biaryl scaffolds by making use of the C3-electrophilicity of 2-indolylmethanols.

摘要

通过 2-萘酚与 2-吲哚甲醇的有机催化不对称偶联反应,首次建立了一类新型轴手性萘基-吲哚骨架的对映选择性构建方法(最高产率 99%,97:3 e.r.)。这种方法不仅提供了一种新型的轴手性杂芳基骨架,而且通过利用 2-吲哚甲醇的 C3-亲电性,为构建轴手性联芳基支架提供了一种新的催化对映选择性策略。

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