Published April 8, 2020
| Supplemental Material
Journal Article
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SeO₂-Mediated Oxidative Transposition of Pauson–Khand Products
Chicago
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Abstract
Oxidative transpositions of bicyclic cyclopentenones mediated by selenium dioxide (SeO₂) are disclosed. Treatment of Pauson–Khand reaction (PKR) products with SeO₂ in the presence or absence of water furnishes di- and trioxidized cyclopentenones, respectively. Mechanistic investigations reveal multiple competing oxidation pathways that depend on substrate identity and water concentration. Functionalization of the oxidized products via cross-coupling methods demonstrates their synthetic utility. These transformations allow rapid access to oxidatively transposed cyclopentenones from simple PKR products.
Additional Information
© 2020 American Chemical Society. Received: January 9, 2020; Published: March 19, 2020. We thank Dr. M. Takase and L. Henling (both of Caltech) for X-ray data collection and Dr. J. Hofstra (Caltech) for X-ray data refinement. Dr. S. Virgil and the Caltech Center for Catalysis and Chemical Synthesis are gratefully acknowledged for access to analytical equipment. Fellowship support was provided by the NSF (S.E.D., M.R.M. Grant No. DGE-1144469). S.E.R. is a Heritage Medical Research Institute Investigator. Financial support from the NIH (R35GM118191-01) is acknowledged. Author Contributions: S.E.D. and M.R.R. contributed equally to this work. The authors declare no competing financial interest. The X-ray crystal structure data for compound 15e was submitted to the Cambridge Crystallographic Data Center, No. 1970101.Attached Files
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Supplemental Material - ja9b13818_si_002.zip
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Additional details
- Eprint ID
- 102000
- Resolver ID
- CaltechAUTHORS:20200319-125552181
- NSF Graduate Research Fellowship
- DGE-1144469
- Heritage Medical Research Institute
- NIH
- R35GM118191-01
- Created
-
2020-03-19Created from EPrint's datestamp field
- Updated
-
2021-11-16Created from EPrint's last_modified field
- Caltech groups
- Heritage Medical Research Institute