期刊
ORGANIC LETTERS
卷 20, 期 6, 页码 1584-1588出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00331
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资金
- National Research Foundation of Korea (NRF) - Korean government (MSIP) [NRF-2016R1A2B3007119, 2016R1A4A1011451]
- National Research Foundation of Korea [2016R1A2B3007119] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
A bioinspired synthesis of chiral 3,4-dihydropyranones via S-to-O acyl-transfer reactions is described. Asymmetric Michael additionlactonization reactions of beta,gamma-unsaturated alpha-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 %.
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