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

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.

SUBMITTER: Lanke V

PROVIDER: S-EPMC6979362 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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

Lanke Veeranjaneyulu V Zhang Fa-Guang FG Kaushansky Alexander A Marek Ilan I

Chemical science 20190827 41

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 selectiv ...[more]

PMID: 32055326

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