Synthesis of 3,3-Disubstituted Thietane Dioxides
4-Membered heterocycles have been increasingly exploited in medicinal chemistry and, as small polar motifs, often show important influence on activity and physicochemical properties. Thietane dioxides similarly offer potential in both agricultural and pharmaceutical applications but are notably understudied. Here we report a divergent approach to 3,3-disubstituted thietane dioxide derivatives by forming carbocations on the 4-membered ring with catalytic Lewis or Brønsted acids. Benzylic tertiary alcohols of the thietane dioxides are coupled directly with arenes, thiols, and alcohols.
Authors
- Juan J. Rojas (ORCID: https://orcid.org/0000-0002-9471-5888)
- James A. Bull (ORCID: https://orcid.org/0000-0003-3993-5818)
- Chulho Choi (ORCID: https://orcid.org/0000-0003-3459-3767)
- Andrew J. P. White (ORCID: https://orcid.org/0000-0001-6175-1607)
- Peerawat Saejong (ORCID: https://orcid.org/0009-0007-4629-5907)
- Jianing Zhong
Institutions
- Pfizer (United States) (US)
- London Biofoundry (GB)
- PRX Research
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-10-11
- DOI
- https://doi.org/10.1021/acs.joc.4c01843
- Citations
- 4
- Primary Topic
- Organic Chemistry Cycloaddition Reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.00
Funders
- Pfizer
- Institute for the Promotion of Teaching Science and Technology
- Royal Society
- Imperial College London