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Updated: Oct 16, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Parts-per-Million-Level, Catalytic [3+2]-Annulations for the Asymmetric Synthesis of Methanobenzo[7]annulenes
Guguloth Thirupathi1, Etikala Ashok1, A Suresh Kumar1
1Catalysis Laboratory, School of Chemistry, University of Hyderabad, Hyderabad, 500 046, India.
Abstract:
3-Alkyl-lawsones selectively reacted with α-alkyl-nitroethylenes under 500 parts-per-million (ppm) quinine-NH-thiourea-catalysis to furnish the chiral methanobenzo[7]annulenes in up to >99 % ee with >20 : 1 dr and TON up to 1820 through tandem Michael/Henry [3+2]-annulations. These asymmetric ppm-level, catalytic tandem [3+2]-annulations would be highly inspirational for the design of many more ppm-level organocatalytic reactions, and at the same time these final molecules are basic skeletons of antibiotics.
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