Journal
CHEMICAL SCIENCE
Volume 13, Issue 1, Pages 170-177Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc05174a
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Funding
- National Natural Science Foundation of China [81972824]
- Guangdong Basic and Applied Basic Research Foundation [2020A1515011513, 2020A1515010684]
- Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery [2019B030301005]
- National Engineering and Technology Research Center for New Drug Druggability Evaluation (Seed Program of Guangdong Province) [2017B090903004]
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A novel method for accessing chiral bis(indolyl)methanes (BIMs) with quaternary stereocenters is developed, showing excellent efficiency and enantioselectivity. The obtained enantioenriched BIMs exhibit practicality through versatile transformations and high antimicrobial activities.
A highly general and straightforward approach to access chiral bis(indolyl)methanes (BIMs) bearing quaternary stereocenters has been realized via enantioconvergent dehydrative nucleophilic substitution. A broad range of 3,3'-, 3,2'- and 3,1'-BIMs were obtained under mild conditions with excellent efficiency and enantioselectivity (80 examples, up to 98% yield and >99 : 1 er). By utilizing racemic 3-indolyl tertiary alcohols as precursors of alkyl electrophiles and indoles as C-H nucleophiles, this organocatalytic strategy avoids pre-activation of substrates and produces water as the only by-product. Mechanistic studies suggest a formal SN1-type pathway enabled by chiral phosphoric acid catalysis. The practicability of the obtained enantioenriched BIMs was further demonstrated by versatile transformation and high antimicrobial activities (3al, MIC: 1 mu g mL(-1)).
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