Access to Optically Pure Benzosultams by Superelectrophilic Activation.
Bastien MicheletUgo CastelliEmeline AppertMaude BoucherKassandra VitseJérôme MarrotJérôme GuillardAgnès Martin-MingotSébastien ThibaudeauPublished in: Organic letters (2020)
Through superacid activation, N-(arenesulfonyl)-aminoalcohols derived from readily available ephedrines or amino acids undergo an intramolecular Friedel-Crafts reaction to afford enantiopure benzosultams bearing two adjacent stereocenters in high yields with fully controlled diastereoselectivity. Low-temperature NMR spectroscopy demonstrated the crucial role played by the conformationally restricted chiral dicationic intermediates.
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