Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel–Crafts alkylation. Issue 41 (30th August 2019)

• Record Type: Journal Article
• Authors: Lanke, Veeranjaneyulu; Zhang, Fa-Guang; Kaushansky, Alexander; Marek, Ilan
• Is Part Of: Chemical science. Volume 10:Issue 41(2019)
• Page Start: 9548
• Page End: 9554
• Publication Date: 2019-08-30
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9sc03832a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : We herein disclose a diastereoselective ring opening of non-donor–acceptor cyclopropanes via an intramolecular Friedel–Crafts alkylation en route to functionalized dihydronaphthalene scaffolds possessing quaternary carbon stereocentres. Abstract : We herein disclose a diastereoselective ring opening of non-donor–acceptor cyclopropanes via an intramolecular Friedel–Crafts alkylation en route to functionalized dihydronaphthalene scaffolds possessing quaternary carbon stereocentres. The transformation proceeds through a selective bond breaking at the most alkylated carbon centre with a pure retention of configuration. Mechanistic investigations and computational studies revealed that alkoxy functionality is the key for selective bond breaking leading to a complete retention of configuration.