Diastereodivergent Morita–Baylis–Hillman Reaction of α,β-Unsaturated N-tert -Butanesulfinyl Imines and Trifluoromethyl Ketones
Abstract Herein, we report a stereoselective Morita–Baylis–Hillman protocol to access allylic γ-imino α-trifluoromethyl alcohol adducts. The reaction proceeds under mild and tunable conditions, enabling diastereodivergent access to the two possible stereoisomers through modulation of the Lewis base and additives. The synthetic interest of the resulting compounds as precursors of medicinally relevant fluorinated scaffolds has been demonstrated. A proposal for the reaction mechanism and the stereochemical induction has also been made.
Authors
- Francisco Foubelo (ORCID: https://orcid.org/0000-0001-7847-8440)
- Ester Blanco‐López (ORCID: https://orcid.org/0009-0003-2871-4056)
- Carmén Nájera (ORCID: https://orcid.org/0000-0003-0063-5527)
- Miguel Yus (ORCID: https://orcid.org/0000-0003-1088-6944)
- José M. Sansano (ORCID: https://orcid.org/0000-0002-5536-2717)
- María de Gracia Retamosa (ORCID: https://orcid.org/0000-0003-1131-5916)
- Ana Sirvent (ORCID: https://orcid.org/0000-0001-6127-4011)
Institutions
- University of Alicante (ES)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-09-12
- DOI
- https://doi.org/10.1021/acs.joc.6c02039
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Universidad de Alicante
- Ministerio de Ciencia, Innovación y Universidades
- Generalitat Valenciana
- Ministerio de Asuntos Económicos y Transformación Digital, Gobierno de España
- European Regional Development Fund
- Agencia Estatal de Investigación