DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes
Herein, we report a DMAP-catalyzed [4 + 2] annulation reaction of hex-5-en-2-ynoates <b>1</b> with electron-poor alkenes <b>2</b>, which affords exocyclic olefinic cyclohexenes <b>3</b> in good yields and excellent regio-, diastereo-, and <i>E</i>/<i>Z</i> selectivities. Distinguished from previous allenoate- or alkynoate-based substrates, hex-5-en-2-ynoates <b>1</b> use the β- and ε-carbons for the bond formation, presenting new and regiodivergent C<sub>4</sub> synthons for Lewis base-catalyzed annulations.
Authors
- Dongqiu Li
- Silong Xu (ORCID: https://orcid.org/0000-0003-3279-9331)
- Lulu Yang (ORCID: https://orcid.org/0000-0002-3979-2522)
- Jiale Wu (ORCID: https://orcid.org/0009-0001-8053-9991)
- Yang Li (ORCID: https://orcid.org/0000-0002-9311-3412)
- Yuhai Tang (ORCID: https://orcid.org/0000-0002-5355-5144)
- Shuangshuang Cai
Institutions
- Northwest Institute of Mechanical and Electrical Engineering (CN)
- Xi'an Jiaotong University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-20
- DOI
- https://doi.org/10.1021/acs.orglett.4c03842
- Citations
- 2
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- National Natural Science Foundation of China
- K. C. Wong Education Foundation
- Fundamental Research Funds for the Central Universities