Enantioselective and Divergent Trienamine-Mediated Reactions of Halogenated Maleimides
Halogenated maleimides can undergo either a [4 + 2] cycloaddition or a [4 + 2]/S<sub>N</sub>2 cascade reaction in an enantioselective and divergent fashion with catalytically formed trienamines. Under mild acidic conditions, [4 + 2] cycloadducts are isolated in good yields with complete diastereoselectivity and high enantioselectivity. With the addition of silver(I) benzoate as a base, a [4 + 2]/S<sub>N</sub>2 cascade reaction is induced, forming tricyclic norcaranes in moderate to good yields and with excellent overall stereoselectivity. The influence of the halogen effect on the cycloaddition was investigated experimentally, revealing a minimal impact.
Authors
- Signe Sofie Pladsbjerg Andresen
- Karl Anker Jørgensen (ORCID: https://orcid.org/0000-0002-3482-6236)
- Jonas Faghtmann (ORCID: https://orcid.org/0000-0003-2920-9804)
- Anne Rask Østergaard
- F. Fritz
Institutions
- Aarhus University (DK)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-05-14
- DOI
- https://doi.org/10.1021/acs.orglett.5c01444
- Citations
- 1
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Aarhus Universitet
- Natur og Univers, Det Frie Forskningsråd
- Villum Fonden
- Novo Nordisk Fonden