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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Bicyclic carbocycles with high Csp³ content are valuable in medicinal chemistry.
  • Previous cycloaddition methods for bicyclobutanes (BCBs) were limited for medium-sized bridged carbocycles.

Purpose of the Study:

  • To develop a novel synthetic route for medium-sized bridged carbocycles.
  • To explore the formal [4+2] cycloaddition of bicyclobutane ketones with silyl dienol ethers.

Main Methods:

  • Utilized bicyclobutane (BCB) ketones and silyl dienol ethers in a formal [4+2] cycloaddition.
  • Employed aluminium triflate as a Lewis acid catalyst (5 mol%).
  • Acidic hydrolysis of enol ether intermediates to yield bicyclo[4.1.1]octane (BCO) diketones.

Main Results:

  • Achieved synthesis of rigid bicyclo[4.1.1]octane (BCO) diketones in up to quantitative yields.
  • Demonstrated tolerance for diverse aromatic and aliphatic substituents on substrates and dienes.
  • Showcased subsequent functionalization of BCO products via reduction and cross-coupling.

Conclusions:

  • Established an efficient Lewis acid-catalyzed method for synthesizing BCO diketones.
  • Expanded the scope of BCB cycloadditions to medium-sized bridged carbocycles.
  • Provided access to versatile BCO scaffolds for further chemical modification.