A General Protocol for the Aqueous Morita‐Baylis‐Hillman Reaction between Cyclic Enones and 1,2‐Dicarbonyl Compounds
Abstract In this report, we present an extensive methodological study of the aqueous Morita–Baylis–Hillman (MBH) reaction of a range of cycloenones with di‐ and tricarbonyl compounds, such as glyoxal derivatives, aliphatic and aromatic α‐keto esters, 1,2‐diketones, diethyl ketomalonate, ninhydrin, acenaphthenequinone, and phenanthrene‐9,10‐dione, through mediation of a bicyclic imidazolyl alcohol (BIA) as catalyst in aqueous medium. The desired MBH adducts were obtained in up to 98 % yield. The synthetic applicability of the MBH adducts was demonstrated by the preparation of an acenaphtho[1,2‐ b ]indole derivative.
Authors
- Ana Julia Senna (ORCID: https://orcid.org/0000-0001-7401-4542)
- Manoel T. Rodrigues (ORCID: https://orcid.org/0000-0001-9230-5642)
- José Cláudio Serafim
- Albert Moyano (ORCID: https://orcid.org/0000-0002-6331-1397)
- Fernando Coelho (ORCID: https://orcid.org/0000-0003-1800-1549)
- Laís V. Acconcia (ORCID: https://orcid.org/0009-0002-4267-8840)
- João Arantes
- Hugo Santos (ORCID: https://orcid.org/0000-0002-7411-5180)
Institutions
- Universidade Estadual de Campinas (UNICAMP) (BR)
- Zero to Three (US)
- Instituto de Química Orgánica General (ES)
- Universitat de Barcelona (ES)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2024-12-11
- DOI
- https://doi.org/10.1002/ejoc.202400852
- Citations
- 3
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.75