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Bioinspired Synthesis of Chiral 3,4-Dihydropyranones via S-to-O Acyl-Transfer Reactions

Hui Jin, Juyeol Lee, Hu Shi, Jin Yong Lee, Eun Jeong Yoo, Choong Eui Song and Do Hyun Ryu*

*Department of Chemistry, Sungkyunkwan University, Suwon 16419, Korea, Email: dhryuskku.edu

H. Jin, J. Lee, H. Shi, J. Y. Lee, E. J. Yoo, C. E. Song, D. H. Ryu, Org. Lett., 2018, 20, 1584-15888.

DOI: 10.1021/acs.orglett.8b00331 (free Supporting Information)


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Abstract

Asymmetric Michael addition-lactonization reactions of β,γ-unsaturated α-keto esters with thioesters catalyzed by a proline-derived urea provide 3,4-dihydropyranones and spiro-3,4-dihydrocoumarin-fused 3′,4′-dihydropyranones in high yield with excellent stereoselectivities via bioinspired S-to-O acyl-transfer reactions.

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Key Words

3,4-Dihydropyranones, Organocatalysis


ID: J54-Y2018