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Issue 48, 2014
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An enantioselective Diels–Alder reaction of 1,2-dihydropyridines with α-acyloxyacroleins catalyzed by a chiral primary ammonium salt

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Abstract

The first enantioselective Diels–Alder reaction of 1,2-dihydropyridines with α-acyloxyacroleins catalyzed by a chiral primary ammonium salt has been developed and it offers more efficient routes to key synthetic intermediates of alkaloids, for which the direct preparations were unavailable before. The asymmetric induction can be understood through the optimized geometry of an iminium salt aqua complex derived from the catalyst and the dienophile.

Graphical abstract: An enantioselective Diels–Alder reaction of 1,2-dihydropyridines with α-acyloxyacroleins catalyzed by a chiral primary ammonium salt

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Publication details

The article was received on 25 Feb 2014, accepted on 10 Apr 2014 and first published on 11 Apr 2014


Article type: Communication
DOI: 10.1039/C4CC01445F
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Chem. Commun., 2014,50, 6357-6360

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    An enantioselective Diels–Alder reaction of 1,2-dihydropyridines with α-acyloxyacroleins catalyzed by a chiral primary ammonium salt

    K. Ishihara, H. Yamada and M. Akakura, Chem. Commun., 2014, 50, 6357
    DOI: 10.1039/C4CC01445F

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