Silyl Lewis Acid-Catalyzed 5-endo-trig Remote Aryl Rearrangement Enabling Dual Migration of Anisole and Amide Groups of N-Cinnamyl-N-alkoxybenzyl Sulfonamides.

A silyl Lewis acid-catalyzed 5-endo-trig remote aryl rearrangement of N-cinnamyl-N-alkoxybenzyl sulfonamides in the presence of an oxidant has been developed, affording 5-substituted oxazolidines in high yields. This reaction proceeds through the dearomatization of the arene moiety on the alkoxybenzyl group. Furthermore, derivatization of the oxazolidine product via terminal carbon-selective ring opening of the corresponding aziridine intermediate with various nucleophiles triggers a dual migration of the anisole and amide moieties, highlighting the broad synthetic potential of this remote aryl rearrangement.

• Publication year

  2025

• Venue

  Organic Letters

• Publication date

  2025-11-09

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.orglett.5c03952PMID 41208240
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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