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Chiral Brønsted Acid‐Catalyzed Asymmetric 1,4‐Addition of Benzofuran‐Derived Azadienes with 3‐Substituted indoles

Zhou Ji, Tian‐Zhen Li, Yu‐Wen Sun, Bai‐Xiang Du, Wei Tan, Feng Shi

2020ChemCatChem36 citationsDOI

Abstract

Abstract A chiral phosphoric acid‐catalyzed asymmetric 1,4‐addition of benzofuran‐derived azadienes with 3‐substituted indoles has been established, which offered enantioenriched tri(hetero)arylmethane products in generally good yields (up to 98 %) and high enantioselectivities (up to 99 : 1 er). This reaction has not only realized the application of chiral phosphoric acid as a competent catalyst in the asymmetric transformations of benzofuran‐derived azadienes, but also has accomplished the task of developing chiral Brønsted acid‐catalyzed asymmetric 1,4‐additions of benzofuran‐derived azadienes, which will enrich the research contents of chiral phosphoric acid catalysis and the chemistry of benzofuran‐derived azadienes.

Topics & Concepts

BenzofuranPhosphoric acidBrønsted–Lowry acid–base theoryCatalysisChemistryEnantioselective synthesisCombinatorial chemistryOrganic chemistryAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality SynthesisAdvanced Synthetic Organic Chemistry
Chiral Brønsted Acid‐Catalyzed Asymmetric 1,4‐Addition of Benzofuran‐Derived Azadienes with 3‐Substituted indoles | Litcius