Switching of regioselectivity in base-mediated diastereoselective annulation of 2,3-epoxy tosylates and their N-tosylaziridine analogs with 2-mercaptobenzimidazole.

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ID: 98843
2020
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Abstract
A base-mediated dinucleophilic cyclization of readily accessible 2,3-epoxy tosylates with 2-mercaptobenzimidazole has been developed for the one-pot diastereoselective synthesis of benzimidazole-based tricyclic compounds equipped with two stereogenic centres. With trans-substrates bearing an aryl or alkyl substituent at the C3 position, the reaction involves an initial S-C1 bond-forming intermolecular alkylation followed by an N-C3 bond-forming, endo-selective intramolecular epoxide ring-opening cyclization reaction. A spectacular regioselectivity switching (tandem S-C3 and N-C1 bond formation reactions) was observed with related trans-N-tosylaziridine substrates. Wide substrate scope, complete diastereoselectivity, high to complete regioselectivity and mild transition metal-free conditions render this protocol particularly efficient and practical.
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das2020switchingorganic Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Das, Arup Jyoti;Borgohain, Hemi;Sarma, Bipul;Das, Sajal Kumar;
Journal Organic & biomolecular chemistry
Year 2020
DOI
10.1039/c9ob02454a
URL
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