Year: 2025
Type: article
Abstract: An asymmetric intramolecular hydride shift reaction has been developed that is catalyzed by Al Lewis acids in conjunction with a chiral BINOL-derived ligand. Racemic THP substrates are transformed into cyclohexene products via a prochiral intermediate ring opened enone; which then undergoes a key 1,5-hydride shift reaction. This reaction is operationally simple, works well on a gram scale, and the desired products are formed with very high enantioselectivity (up to >98:2 e.r.). Importantly, the cyclohexene products contain functionality that can be easily derivatized and this is exemplified in the paper. Finally, a model is presented for the enantioselective hydride shift that is based on previous DFT studies.
Institution: University of Oxford
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $5,510
OpenAlex ID: W4417459740