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Bioinspired Synthesis of Chiral 3,4-Dihydropyranones via S-to-O Acyl-Transfer Reactions.
- Source :
-
Organic letters [Org Lett] 2018 Mar 16; Vol. 20 (6), pp. 1584-1588. Date of Electronic Publication: 2018 Feb 27. - Publication Year :
- 2018
-
Abstract
- A bioinspired synthesis of chiral 3,4-dihydropyranones via S-to-O acyl-transfer reactions is described. Asymmetric Michael addition-lactonization reactions of β,γ-unsaturated α-keto esters with thioesters are catalyzed by proline-derived urea, providing 3,4-dihydropyranones and spiro-3,4-dihydrocoumarin-fused 3',4'-dihydropyranones in high yield (up to 94%) with excellent stereoselectivities (up to >20:1 dr, 99% ee) under catalyst loadings as low as 1 mol %.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 20
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 29484883
- Full Text :
- https://doi.org/10.1021/acs.orglett.8b00331