Indium Mediated Reformatsky-Type Allylation of N-<i>tert</i>-Butanesulfinyl Iminoester with 1,3-Butadiene
This study presents the indium-mediated three-component radical Reformatsky-type allylation of <i>N</i>-<i>tert</i>-butanesulfinyl iminoester with 1,3-butadiene. This novel approach offers a rapid synthesis pathway to valuable homoallylic noncanonical amino acids, demonstrated with over 30 examples showing nice regio- and diastereoselectivity. Mechanism studies revealed that allylindium complexes served as key intermediates, formed through a single-electron reduction of allylic radicals by Indium species.
Authors
- Yongfa Zhu (ORCID: https://orcid.org/0000-0001-8528-509X)
- Lei Shi (ORCID: https://orcid.org/0000-0002-2644-1168)
- Er‐Jun Hao (ORCID: https://orcid.org/0000-0001-5821-8465)
- Zhixian Wu (ORCID: https://orcid.org/0000-0002-0708-6770)
- Qingyu Shi (ORCID: https://orcid.org/0009-0004-8225-0958)
- Yunhe Jin (ORCID: https://orcid.org/0000-0003-0626-4587)
- Xuehan Qi
- Y. J. Mao (ORCID: https://orcid.org/0000-0002-5627-5199)
- Renxu Cao
- Shuangjie Lin
- Shaohua Zhang (ORCID: https://orcid.org/0009-0004-3950-8503)
Institutions
- Dalian University of Technology (CN)
- Henan Normal University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-20
- DOI
- https://doi.org/10.1021/acs.orglett.4c04086
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Henan Province