Double Hydride Transfer Enabled Substitution of All Hydrogens at α,β-Positions of Cyclic Amines: Access to α,β-Unsaturated Lactams
A one-shot substitution of all hydrogens at the α,β-positions of saturated cyclic amines was achieved. The key feature of this reaction is the sequential involvement of intra- and intermolecular redox processes. When <i>N</i>,<i>O</i>-acetals obtained through an internal redox process were treated with a catalytic amount of Zn(OTf)<sub>2</sub> and an excess amount of benzylidene barbiturates, three key transformations involving intermolecular redox process occurred successively to afford α,β-unsaturated lactams in moderate to good chemical yields.
Authors
- Keiji Mori (ORCID: https://orcid.org/0000-0002-9878-993X)
- Ryosuke Yamagishi
- Masahiro Anada (ORCID: https://orcid.org/0000-0002-7691-5114)
- Tatsuhiro Kojima (ORCID: https://orcid.org/0000-0002-1313-8987)
- Tomoko Kawasaki‐Takasuka (ORCID: https://orcid.org/0000-0002-8468-7553)
- Shunsuke Sueki (ORCID: https://orcid.org/0000-0003-0951-0018)
- Kosho Makino (ORCID: https://orcid.org/0000-0001-8635-6793)
Institutions
- Musashino University (JP)
- Kobe City College of Technology (JP)
- Tokyo University of Agriculture and Technology (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-13
- DOI
- https://doi.org/10.1021/acs.orglett.5c00255
- Citations
- 4
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- Naito Foundation