Abstract
An enantioselective addition of arylboronic acids and α-ketoesters promoted by a Rhodium(I)-chiral diene catalyst is reported. The transformation proceeds regioselectively in the presence of as low as 0.5 mol% of the catalyst generated in situ from a Rhodium(I) salt and diene L1, which is a bicyclo[2.2.1] ligand scaffold bearing 2,5 dinaphthyl substituents, to afford tertiary chiral α-hydroxy esters with high stereoselectivities (90–99% ee's) and in 50–>99% yields. The method provides an expeditious and enantioselective synthesis of (S)-flutriafol. (Figure presented.).
| Original language | English |
|---|---|
| Pages (from-to) | 3381-3390 |
| Number of pages | 10 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 360 |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - 2018 Sep 3 |
Keywords
- arylation
- asymmetric catalysis
- rhodium
- tertiary α-hydroxy esters
- α-ketoesters
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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Chang, C. A., Uang, T. Y., Jian, J. H., Zhou, M. Y., Chen, M. L., Kuo, T. S., Wu, P. Y., & Wu, H. L. (2018). Efficient and Enantioselective Rhodium(I)-Catalyzed Arylation of α-Ketoesters: Synthesis of (S)-Flutriafol. Advanced Synthesis and Catalysis, 360(17), 3381-3390. https://doi.org/10.1002/adsc.201800575