Lewis Acid-Catalyzed Ring-Opening Reaction of Bicyclobutanes (BCBs) for the Highly Selective Synthesis of 1,1,3-Trisubstituted Cyclobutanes.

Herein, the first Lewis acid-catalyzed ring-opening reaction of bicyclobutanes (BCBs) with acyclic thioamides for the concise, modular synthesis of 1,1,3-trisubstituted cyclobutanes is described. These products feature valuable iminothioether-substituted cyclopropane moieties and single-configuration tetrasubstituted carbon stereocenters. The reaction proceeds under mild conditions and accommodates diverse acyclic thioamides and substituted acyl-BCBs, exhibiting excellent nucleophilic selectivity (S-H/N-H > 99/1) and chemoselectivity (trans/cis > 98/2). Derivatization experiments and single-crystal X-ray structural analysis further confirmed the synthetic utility of this reaction.

• Publication year

  2025

• Venue

  Organic Letters

• Publication date

  2025-08-19

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.orglett.5c02896PMID 40831044
• 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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