Application of β-Keto Acylpyrazoles as 2C Synthons in Asymmetric Cyclizations of <i>ortho</i>-Hydroxychalcones: Stereoselective Construction of <i>trans</i>-3,4-Dihydrocoumarins
An asymmetric tandem esterification/Michael addition reaction of β-keto acylpyrazoles with <i>o</i>-hydroxychalcones has been established under the catalysis of a bifunctional squaramide-tertiary amine. A wide variety of biorelevant 3,4-dihydrocoumarin derivatives were generally obtained in high yields (up to 93%) with excellent diastereo- and enantioselectivities (>19:1 dr, up to 93% ee) under mild reaction conditions. This reaction represents the successful application of β-keto acylpyrazoles as 2C building blocks in catalytic asymmetric cyclizations.
Authors
- Zhenghong Zhou (ORCID: https://orcid.org/0000-0001-7753-4236)
- Changchun Yuan (ORCID: https://orcid.org/0000-0002-2889-4566)
- Liying Cui
- Xiaofeng Yang (ORCID: https://orcid.org/0000-0001-9574-0826)
Institutions
- North University of China (CN)
- Nankai University (CN)
- Collaborative Innovation Center of Chemical Science and Engineering Tianjin (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-12-10
- DOI
- https://doi.org/10.1021/acs.joc.4c01327
- Citations
- 5
- Primary Topic
- Synthesis of Indole Derivatives
- Type
- article
- Field-Weighted Citation Impact
- 1.25
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Shanxi Province
- National Key Research and Development Program of China