Catalyst-Controlled Diastereoselective Synthesis of Bridged [3.3.1] Bis(Indolyl)-Oxanes and Oxepanes via Desymmetrization of Bis(Indolyl)-Cyclohexadienones
Abhishek Kumar Mishra, Anil Chauhan, Santosh Kumar, Ruchir Kant, Ravindra Kumar
Abstract
A catalyst-controlled divergent synthesis of bridged [3.3.1] bis(indolyl)-oxanes and cis -[6.7] fused bis(indolyl) oxepanes via diastereoselective desymmetrization of bis(indolyl)-cyclohexadienones is presented for the first time. The reaction is highly atom- and step-economic, furnishing sp 3 -rich functionalized bis(indolyl) derivatives in good to excellent yields with wide substrate scope. The reaction proceeds through Friedel–Crafts alkylation followed by catalyst-controlled selective C–C bond formation/rearrangement. Gram scale synthesis and synthetic utility to generate bis(indolyl) alkaloid-like molecular diversity were also illustrated.
Topics & Concepts
DesymmetrizationChemistryCatalysisMedicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryEnantioselective synthesisSynthesis of Indole DerivativesAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality Synthesis