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Researchers developed a new method for synthesizing seven- and five-membered rings using a hydride shift and cyclization. Different catalysts, ytterbium(III) triflate and scandium(III) triflate, selectively produced either benzoxepines or indanes, respectively.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Accessing diverse heterocyclic scaffolds is crucial in organic synthesis.
  • Controlling ring size selectivity in cyclization reactions remains a challenge.

Purpose of the Study:

  • To develop a divergent synthetic route to seven- and five-membered rings.
  • To investigate the influence of Lewis acid catalysts on regioselectivity in cyclization.

Main Methods:

  • Utilizing a [1,6]-hydride shift/cyclization cascade reaction.
  • Employing benzylidenemalonate derivatives with ortho-alkoxymethyl substituents.
  • Exploring the catalytic activity of ytterbium(III) triflate (Yb(OTf)3) and scandium(III) triflate (Sc(OTf)3).

Main Results:

  • Achieved divergent synthesis of seven-membered benzoxepines selectively using Yb(OTf)3.
  • Obtained five-membered indanes as the main products when using Sc(OTf)3.
  • Demonstrated a catalyst-controlled divergent pathway based on a single precursor.

Conclusions:

  • The [1,6]-hydride shift/cyclization strategy provides versatile access to different ring sizes.
  • Lewis acid selection is key to controlling the outcome of the cyclization, enabling selective formation of benzoxepines or indanes.
  • This methodology offers an efficient route to valuable heterocyclic compounds.