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Article Dans Une Revue Organic Letters Année : 2020

Access to Optically-Pure Benzosultams by Superelectrophilic Activation

Résumé

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 a fully-controlled diastereoselectivity. Low-temperature NMR spectroscopy demonstrated the crucial role played by the conformationally-restricted chiral dicationic intermediates.

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Chimie
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Dates et versions

hal-03016554 , version 1 (20-11-2020)

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Bastien Michelet, Ugo Castelli, Emeline Appert, Maude Boucher, Kassandra Vitse, et al.. Access to Optically-Pure Benzosultams by Superelectrophilic Activation. Organic Letters, 2020, 22 (13), pp.4944-4948. ⟨10.1021/acs.orglett.0c01301⟩. ⟨hal-03016554⟩
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