Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel-Crafts alkylation: Via intramolecular Friedel-Crafts alkylation

Veeranjaneyulu Lanke, Fa-Guang Zhang, Alexander Kaushansky, Ilan Marek

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)9548-9554
Number of pages7
JournalChemical Science
Volume10
Issue number41
DOIs
StatePublished - 7 Nov 2019

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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