Enantioselective Synthesis of Highly Functionalized 2,3-Dihydrobenzofuran Derivatives via Steric Hindrance-Overcoming Strategy
The asymmetric cycloaddition reaction of <i>p</i>-quinone monoimides is a significant research focus for constructing benzofused heterocycles. However, due to steric effects, achieving efficient cycloaddition at highly sterically hindered site is challenging but practically valuable. Herein, we develop an asymmetric [3 + 2] cycloaddition reaction of <i>p</i>-quinone monoimides with 1-vinylnaphthalen-2-ols and 3-vinylindoles via steric hindrance-overcoming strategy. Binaphthalene-based chiral phosphoric acid catalyzes the asymmetric cycloaddition reaction to synthesize highly functionalized 2,3-dihydrobenzofurans in generally good yields with good to excellent stereoselectivities.
Authors
- Yang Lei (ORCID: https://orcid.org/0000-0003-0709-4743)
- Jian‐Qiang Zhao (ORCID: https://orcid.org/0000-0002-4444-9630)
- Zhen‐Hua Wang (ORCID: https://orcid.org/0000-0002-0603-707X)
- Shubin Wu (ORCID: https://orcid.org/0000-0002-2663-3397)
- Wei‐Cheng Yuan (ORCID: https://orcid.org/0000-0003-4850-8981)
- Hui Zhang (ORCID: https://orcid.org/0000-0002-0756-9334)
- Yanping Zhang (ORCID: https://orcid.org/0000-0002-4190-7026)
- Dong-Qun Huang
- Yong You (ORCID: https://orcid.org/0000-0002-4689-0235)
Institutions
- Changzhi Medical College (CN)
- Chengdu University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-06-06
- DOI
- https://doi.org/10.1021/acs.joc.5c00764
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Department of Science and Technology of Sichuan Province