Organocatalytic cascade reaction of aliphatic enals and benzoylnitromethane: synthesis of enantioenriched tetrasubstituted cyclohexene carbaldehyde
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2020
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Journal of chemistry, 2090-9071, Vol. 2020
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Hindawi
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A new example of the reactivity of enals with benzoylnitromethane was studied in a Michael-Michael-Aldol-Dehydration quadruple organocascade reaction. The reaction unexpectedly yielded a tetrasubstituted cyclohexene carbaldehyde with excellent enantiomeric excess when crotonaldehyde was used as the Michael-acceptor, whereas using (E)-Hex-2-enal as the Michael-acceptor formed a cyclic hemiacetal by steering the reaction into the intramolecular formation of the same intermediate via a Michael-Heterocyclization domino reaction.
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