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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel-Crafts alkylation
Veeranjaneyulu Lanke1, Fa-Guang Zhang1, Alexander Kaushansky1
1Schulich Faculty of Chemistry , Technion - Israel Institute of Technology , Technion City 3200009 , Haifa , Israel .
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.
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