Document Type
Article
Publication Date
10-27-2023
Abstract
We report an enantioselective synthesis of cyclic ketones with full substitutions at the α-positions in a highly diastereoselective manner. Our method is achieved by subjecting substrate motifs in 2-allyloxyenones to chiral organomagnesium reagents, which trigger the Claisen rearrangement upon direct 1,2-carbonyl addition. The observed diastereoselectivity of the allyl migration is proposed to originate from the intramolecular chelation of the magnesium alkoxide to the allyloxy moiety.
Publication Source (Journal or Book title)
Organic Letters
First Page
7622
Last Page
7627
Recommended Citation
Badmus, F., Thombal, R., Philkhana, S., Malone, J., Bailey, C., Armendariz-Gonzalez, E., Mureka, E., Locicero, C., Fronczek, F., & Kartika, R. (2023). Directing the Stereoselectivity of the Claisen Rearrangement to Form Cyclic Ketones with Full Substitution at the α-Positions. Organic Letters, 25 (42), 7622-7627. https://doi.org/10.1021/acs.orglett.3c02752