Highly Efficient One-Pot Synthesis of 2,4,5-Trisubstituted 3(2<i>H</i>)-Furanones Utilizing a Au(I)-Catalyzed Oxidation/Pinacol Rearrangement/<i>anti</i>-Michael Cascade
A highly efficient Au(I)-catalyzed cascade reaction between bispropargylic alcohols and pyridine-<i>N</i>-oxides has been realized. The reaction process involved a gold(I)-catalyzed sequential oxidation/Pinacol rearrangement/oxacyclization. Moreover, 1,2-aryl, 1,2-alkyl, or 1,2-vinyl migration was favored over 1,2-alkynyl in the crucial gold(I)-catalyzed Pinacol rearrangement step. A range of 2,4,5-trisubstituted 3(2<i>H</i>)-furanones were synthesized in high yields (up to 88%) with excellent regioselectivities (up to >19:1) under mild reaction conditions.
Authors
- Jianfeng Zheng (ORCID: https://orcid.org/0000-0002-3330-548X)
- Shuang Zang
- Lingyao Wang (ORCID: https://orcid.org/0000-0001-8584-8358)
- Lichun Kong
- Jun Li (ORCID: https://orcid.org/0000-0001-8524-4634)
- Hang Ren (ORCID: https://orcid.org/0009-0008-0442-8457)
- Yanbin Wu
Institutions
- Zhejiang Normal University (CN)
- Ministry of Education (PT)
- Southwest Jiaotong University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-03
- DOI
- https://doi.org/10.1021/acs.orglett.4c02760
- Citations
- 2
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- National Natural Science Foundation of China
- Zhejiang Normal University