Organocatalytic approach to 3,5,6-trisubstituted and 4,6-disubstituted tetrahydropyran-2-ones |
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| Authors: | Danhua Xu Dawei Ma |
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| Affiliation: | a Center of Drug Discovery, China Pharmaceutical University, Nanjing 210009, China
b State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China |
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| Abstract: | The diarylprolinol ether-catalyzed Michael addition and subsequent cyclization of ethyl 3-methyl-2-oxobut-3-enoate with aldehydes, and γ-substituted β,γ-unsaturated-α-ketoesters with acetaldehyde, afforded the corresponding lactals, which were subjected to oxidation and stereocontrolled hydrogenation to provide 3,5,6-trisubstituted and 4,6-disubstituted tetrahydropyran-2-ones with excellent enantioselectivities. |
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