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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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Article information


Submitted
25 Feb 2014
Accepted
10 Apr 2014
First published
11 Apr 2014

Chem. Commun., 2014,50, 6357-6360
Article type
Communication
Author version available

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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