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- W2017221913 abstract "Anthrone has been found to react with N-methylmaleimide in the presence of catalytic amounts of various chiral β-aminoalcohols. The cycloadduct 3a has been obtained in excellent yield with enantiomeric excess of up to 61%. Its absolute configuration has been assigned by X-ray crystallography. Several features of the reaction have been studied: variation of dienophile; competition between cycloaddition and formation of the optically active Michael adduct 4; solvent and temperature effects. Mechanistic studies are in agreement with a concerted [4+2] process, providing an unique case of a base-catalyzed asymmetric Diels-Alder reaction. Anthrone with N-methylmaleimide in presence of various β-aminoalcohols to give 3a. Several features of this base-catalyzed Diels-Alder reaction have been studied. Quinidine leads to optically active 3a (ee up to 61%) whose absolute configuration has been established." @default.
- W2017221913 created "2016-06-24" @default.
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- W2017221913 date "1994-04-01" @default.
- W2017221913 modified "2023-09-26" @default.
- W2017221913 title "Asymmetric base-catalyzed cycloaddition between anthrone and some dienophiles" @default.
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- W2017221913 doi "https://doi.org/10.1016/s0040-4020(01)89385-6" @default.
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