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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Radical Cyclization/β-Elimination Tandem Reactions: Enantiopure Sulfoxides as Temporary Chiral Auxiliaries
Emmanuel Lacôte1, Bénédicte Delouvrié1, Louis Fensterbank1
1Laboratoire de Chimie Organique de Synthèse, associé au CNRS, Université Pierre et Marie Curie, 4, place Jussieu, Tour 44-54, Case 229 F-75252 Paris Cedex 05 (France), Fax: (+33) 1-44-27-73-60.
Abstract:
Alkylidene-substituted cyclopentane derivatives are formed in high enantiomeric purity by the reaction shown below. A highly diastereoselective radical cyclization is followed by elimination of a β-sulfinyl radical. Interestingly, the addition of the Lewis acid methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD) totally reverses the stereochemical outcome of the reaction. E=CO2 Me.
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