4.8 Article

Asymmetric Diels-Alder reactions of 2-pyrones with a bifunctional organic catalyst

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 129, 期 20, 页码 6364-+

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AMER CHEMICAL SOC
DOI: 10.1021/ja070859h

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  1. NIGMS NIH HHS [GM 61591, R01 GM061591, R01 GM061591-07] Funding Source: Medline

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The reactions of 2-pyrones with electron-deficient dienophiles constitute a synthetically useful class of Diels-Alder reaction. By exploring cinchona alkaloid-derived organic molecules as acid-base bifunctional catalysts, we successfully developed the first highly enantioselective and diastereoselective catalytic Diels-Alder reaction with 2-pyrones. Furthermore, we demonstrated the possibility of using such catalysts to control the endo/exo selectivity in a Diels-Alder reaction.

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