Abstract
A Rh-catalyzed asymmetric intramolecular Buchner ring expansion of α-alkyl-α-diazoesters has been developed. The present protocol generates a 5,7-fused ring system in an enantioselective manner while minimizing β-hydrogen migration, which has been a competing reaction when using α-alkyl-α-diazoesters. The ester functionality at the bridgehead position would be a useful synthetic handle for further derivatization to complex molecules including natural products.
| Original language | English |
|---|---|
| Pages (from-to) | 10081-10084 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 21 |
| Issue number | 24 |
| DOIs | |
| Publication status | Published - 2019 Dec 20 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Hoshi, T., Ota, E., Inokuma, Y., & Yamaguchi, J. (2019). Asymmetric Synthesis of a 5,7-Fused Ring System Enabled by an Intramolecular Buchner Reaction with Chiral Rhodium Catalyst. Organic Letters, 21(24), 10081-10084. https://doi.org/10.1021/acs.orglett.9b04048