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 language | English |
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Pages (from-to) | 9548-9554 |
Number of pages | 7 |
Journal | Chemical Science |
Volume | 10 |
Issue number | 41 |
DOIs | |
State | Published - 7 Nov 2019 |
All Science Journal Classification (ASJC) codes
- Chemistry(all)