Substituents Regulate the Cyclization of Conjugated Alkynes to Accurately Construct Cyclo-(E)-[3]dendralenes

Molecules. 2023 May 27;28(11):4382. doi: 10.3390/molecules28114382.

Abstract

Substituent-regulated cyclization of conjugated alkynes with acid catalysis was developed in this paper, and it provides a straightforward synthesis of cyclic-(E)-[3]dendralenes. Depending on the electronic effect of the aromatic ring pairing, a variety of phosphinyl quintuplet/hexa cyclo-[3]dendralenes with diverse substitution patterns are accessible, with good efficiency and high stereoselectivity. This self-cyclization process achieves the first precise construction of a phosphinylcyclo-(E)-[3]dendralene from conjugated alkynes to aromatization.

Keywords: conjugated alkynes; cyclization; cyclo-[3]dendralenes; substituents regulate.

MeSH terms

  • Alkenes*
  • Alkynes*
  • Catalysis
  • Cyclization
  • Molecular Structure

Substances

  • 3,4,5-trimethylenehepta-1,6-diene
  • Alkynes
  • Alkenes