Three-Component Reaction of Cyclopropanols, DABSO, and <i>N</i>-(Sulfonyl)acrylamides: Preparation of Sulfone-Bridged 1,7-Dicarbonyl Compounds
A cascade reaction of cyclopropyl alcohols, DABSO (1,4-diazoniabicyclo[2.2.2]octane-1,4-disulfinate), and <i>N</i>-(sulfonyl)acrylamides has been developed. This tandem process went through a cyclopropanol ring opening and Michael addition sequence. The γ-keto sulfinate generated from the reaction between cyclopropanol and DABSO serves as the nucleophilic reagent, and <i>N</i>-(sulfonyl)acrylamide is used as the Michael addition acceptor. By utilizing this strategy, multitudinous sulfone-bridged 1,7-dicarbonyl compounds that contain both a β-sulfonyl amide unit and γ-keto sulfone skeleton were conveniently synthesized.
Authors
- Yunhe Lv (ORCID: https://orcid.org/0000-0001-5804-7475)
- Kai Sun (ORCID: https://orcid.org/0000-0002-0041-6044)
- Chenlu Wang (ORCID: https://orcid.org/0000-0003-0232-3447)
- Zheng Yang (ORCID: https://orcid.org/0000-0002-3352-9440)
- Shu-Man Wang
- Fei Chen (ORCID: https://orcid.org/0000-0001-5145-6073)
- Xiao Li (ORCID: https://orcid.org/0000-0002-5238-6393)
- Ke-Ying Liu
- Yu-Xin Lai
- Liu-Yan You
- Dong-Wang He
- Shuliao Tian (ORCID: https://orcid.org/0009-0005-1968-0223)
- Jun-Ya Guo
Institutions
- Yantai University (CN)
- Anyang Normal University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-08-19
- DOI
- https://doi.org/10.1021/acs.orglett.4c02613
- Citations
- 12
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 3.00
Funders
- National Natural Science Foundation of China
- Foundation of Henan Educational Committee
- Natural Science Foundation of Henan Province
- Anyang Normal University