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Angew Chem Int Ed Engl. 2013 Oct 11;52(42):11088-91. doi: 10.1002/anie.201304969. Epub 2013 Aug 28.

Highly enantioselective aza-Diels-Alder reaction of 1-azadienes with enecarbamates catalyzed by chiral phosphoric acids.

Author information

1
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France).

Abstract

On demand: A highly enantio- and diastereoselective synthesis of 6-amino- trisubstituted tetrahydropyridine compounds has been developed through the inverse-electron-demand aza-Diels-Alder reaction of N-aryl α,β-unsaturated ketimines with enecarbamates (E)-1. Chiral phosphoric acid catalysts achieve simultaneous activation of both the 1-azadiene and dienophile partners.

KEYWORDS:

cycloaddition; dienes; heterocycles; organocatalysis; synthetic methods

PMID:
24038965
DOI:
10.1002/anie.201304969
[Indexed for MEDLINE]

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