A highly enantioselective Brønsted acid catalyzed reaction cascade

Magnus Rueping; Andrey P. Antonchick

doi:10.1002/anie.200801435

A highly enantioselective Brønsted acid catalyzed reaction cascade

Magnus Rueping^*, Andrey P. Antonchick

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

116 Scopus citations

Abstract

(Chemical Equation Presented) One cat. is enough! A highly enantiose-lective reaction has been developed for the three-component reaction of an enamine with a vinyl ketone and a Hantszsch ester in which each of the six reaction steps is catalyzed by the same chiral Brønsted acid (see scheme). This reaction offers efficient access to tetrahydropyridines and azadecalinones from simple and readily available starting materials.

Original language	English (US)
Pages (from-to)	5836-5838
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	31
DOIs	https://doi.org/10.1002/anie.200801435
State	Published - Jul 21 2008
Externally published	Yes

Keywords

Michael reaction
Organocatalysis
Phosphates
Piperidines
Reductive amination

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200801435

Cite this

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abstract = "(Chemical Equation Presented) One cat. is enough! A highly enantiose-lective reaction has been developed for the three-component reaction of an enamine with a vinyl ketone and a Hantszsch ester in which each of the six reaction steps is catalyzed by the same chiral Br{\o}nsted acid (see scheme). This reaction offers efficient access to tetrahydropyridines and azadecalinones from simple and readily available starting materials.",

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AU - Antonchick, Andrey P.

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N2 - (Chemical Equation Presented) One cat. is enough! A highly enantiose-lective reaction has been developed for the three-component reaction of an enamine with a vinyl ketone and a Hantszsch ester in which each of the six reaction steps is catalyzed by the same chiral Brønsted acid (see scheme). This reaction offers efficient access to tetrahydropyridines and azadecalinones from simple and readily available starting materials.

AB - (Chemical Equation Presented) One cat. is enough! A highly enantiose-lective reaction has been developed for the three-component reaction of an enamine with a vinyl ketone and a Hantszsch ester in which each of the six reaction steps is catalyzed by the same chiral Brønsted acid (see scheme). This reaction offers efficient access to tetrahydropyridines and azadecalinones from simple and readily available starting materials.

KW - Michael reaction

KW - Organocatalysis

KW - Phosphates

KW - Piperidines

KW - Reductive amination

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ER -

A highly enantioselective Brønsted acid catalyzed reaction cascade

Abstract

Keywords

ASJC Scopus subject areas

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