Synthesis of Chiral 4-Alkyl-3,4-dihydrocoumarins via Rh-Catalyzed Asymmetric Arylation and Acid-Promoted Transesterification
Catalytic asymmetric synthesis of 4-alkyl-3,4-dihydrocoumarins via the construction of the dihydrocoumarin core is reported. Rhodium-catalyzed asymmetric arylation of α,β-unsaturated esters with <i>o</i>-hydroxyl arylboronic acids followed by intramolecular transesterification leads to the production of a series of 4-alkyl-3,4-dihydrocoumarins in high yields with excellent enantioselectivities (most >99% ee). The utility of the method is demonstrated by efficient synthesis of drug candidate R106578.
Authors
- Xiaowei Dou (ORCID: https://orcid.org/0000-0002-0748-1279)
- Junhao Xing
- Weijun Yao (ORCID: https://orcid.org/0000-0001-6463-2937)
- Huihui Zhang (ORCID: https://orcid.org/0000-0002-2541-9022)
- Zhihang Chen (ORCID: https://orcid.org/0000-0003-3843-2047)
- Guanghui Lin (ORCID: https://orcid.org/0000-0002-5078-6254)
Institutions
- Zhejiang Sci-Tech University (CN)
- China Pharmaceutical University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-05-08
- DOI
- https://doi.org/10.1021/acs.joc.5c00579
- Citations
- 5
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 4.68
Funders
- National Natural Science Foundation of China
- Fundamental Research Funds for the Central Universities