Vinyl Sulfonium Reagent Useful for the One-step Synthesis of Spirooxetane Skeleton

Spirooxetane scaffolds are strained hetero rings, which greatly affects the rigidity, hydrophilicity, hydrogen bond acceptance by introduction to the target compounds.¹⁾ Therefore, reagents for oxetane synthesis are attracting more and more attention in drug discovery research.
Dineopentylvinylsulfonium trifluoromethanesulfonate (1) is used in the synthesis of oxetane with easily available alcohols under photoredox conditions through hydrogen atom transfer (HAT) and addition-elimination process.²⁾ 1 is useful for one-step synthesis of oxetanes, typically difficult to obtain by conventional methods, and for convenient introduction of oxetane scaffolds into drugs in late stages. So, 1 helps diversification of molecular structure in R&D process.

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References

• 1) Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry
  • J. A. Bull, R. A. Croft, O. A. Davis, R. Doran, K. F. Morgan, Chem. Rev. 2016, 116, 12150.
• 2) Oxetane Synthesis via Alcohol C−H Functionalization
  • S. Paul, D. Filippini, F. Ficarra, H. Melnychenko, C. Janot, M. Silvi, J. Am. Chem. Soc. 2023, 145, 15688.

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