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Directing the Stereoselectivity of the Claisen Rearrangement to Form Cyclic Ketones with Full Substitution at the α-Positions.
- Source :
-
Organic letters [Org Lett] 2023 Oct 27; Vol. 25 (42), pp. 7622-7627. Date of Electronic Publication: 2023 Oct 13. - Publication Year :
- 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.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 25
- Issue :
- 42
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 37830497
- Full Text :
- https://doi.org/10.1021/acs.orglett.3c02752