Visible‐Light‐Enabled Dual‐Catalysis Approach to Stereoselective [2+2] Cycloaddition of Erlenmeyer‐Plöchl Azlactones
Abstract Visible‐light‐driven dual catalysis was employed to stereoselectively produce densely substituted cyclobutanes from Erlenmeyer‐Plöchl azlactones. The single‐step preparation of non‐natural amino acid dimers containing the cyclobutane moiety was achieved through a synergy between iridium photocatalysis and catalytic nickel(II) triflate as a Lewis acid. The desired 1,2‐( zeta )‐ Z , E ‐isomers were isolated in good yields and with high regio‐ and diastereoselectivity (in all cases, >19 : 1 d.r.). To the best of our knowledge, this is the first report of direct access to truxinic acid analogues using azlactones. Control experiments, EPR reaction monitoring, and DFT calculations suggest that the presence of a Lewis acid, combined with the use of powerful blue LEDs, plays a crucial role in the reactivity of this reaction.
Authors
- Hélio F. Dos Santos (ORCID: https://orcid.org/0000-0003-0196-2642)
- Isabella F. S. Marra
- Kléber T. de Oliveira (ORCID: https://orcid.org/0000-0002-9131-4800)
- Paulo Eduardo Narcizo de Souza (ORCID: https://orcid.org/0000-0002-4289-8678)
- Pedro P. de Castro (ORCID: https://orcid.org/0000-0002-3018-3130)
- Larissa P. Silva (ORCID: https://orcid.org/0000-0002-5832-3844)
- Brenno A. D. Neto (ORCID: https://orcid.org/0000-0003-3783-9283)
- Giovanni W. Amarante (ORCID: https://orcid.org/0000-0003-1004-5395)
- Leonã S. Flôres
Institutions
- Universidade Federal de Juiz de Fora (BR)
- Universidade de Brasília (BR)
- Universidade Federal de São Carlos (BR)
- Instituto Federal de Educação, Ciência e Tecnologia de Brasília (BR)
Publication Details
- Journal
- Asian Journal of Organic Chemistry
- Published
- 2024-08-16
- DOI
- https://doi.org/10.1002/ajoc.202400271
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.21
Funders
- Fundação de Amparo à Pesquisa do Estado de São Paulo
- Conselho Nacional de Desenvolvimento Científico e Tecnológico
- Fundação de Amparo à Pesquisa do Estado de Minas Gerais