Diastereoselective Synthesis of Oxabicyclo[3.3.1]nonenes from Aldehydes and α‐Pinene: Fe(III) Aggregate Catalysis.

  • Published In: Advanced Synthesis & Catalysis, 2025, v. 367, n. 9. P. 1 1 of 3

  • Database: Academic Search Ultimate 2 of 3

  • Authored By: Todtz, Sophi R.; Das, Soumik; Zimmerman, Paul M.; Devery, James J. 3 of 3

Abstract

A challenge for the acid‐mediated formation of oxabicyclo[3.3.1]nonenes is side product formation. Presented herein is a Lewis acid‐catalyzed method towards these structures from aldehydes and α‐pinene, forming the endo diastereomer exclusively. We include a proposal for the stereochemical reassignment of previously reported exo diastereomers supported by density functional theory (DFT) calculations, 1H NMR, and X‐ray crystallography. The reactive system includes a range of aldehyde substrates. Experimental observations along with quantum chemical simulations suggest that an Fe(III)‐aldehyde aggregate functions as the active catalyst. [ABSTRACT FROM AUTHOR]

Additional Information

  • Source:Advanced Synthesis & Catalysis. 2025/05, Vol. 367, Issue 9, p1
  • Document Type:Article
  • Subject Area:Chemistry
  • Publication Date:2025
  • ISSN:1615-4150
  • DOI:10.1002/adsc.202401329
  • Accession Number:185185952
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