Asymmetric Base-catalyzed Cycloaddition Between Anthrone and some Dienophiles
(1994) Tetrahedron — Vol. 50, n° 15, p. 4543-4554 (1994)
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- 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.
- Affiliations
Imperial College (UK) Organic Chemistry
Citations
Riant, O., & Kagan, H. B. (1994). Asymmetric Base-catalyzed Cycloaddition Between Anthrone and some Dienophiles. Tetrahedron, 50(15), 4543-4554. https://doi.org/10.1016/S0040-4020(01)89385-6 (Original work published 1994)