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Asymmetric synthesis of tetrahydropyridines via an organocatalytic one-pot multicomponent Michael/aza-Henry/cyclization triple domino reaction.

ABSTRACT: A low loading of a quinine-derived squaramide efficiently catalyzes the triple-domino Michael/aza-Henry/cyclization reaction between 1,3-dicarbonyl compounds, ?-nitroolefins, and aldimines to provide tetrahydropyridines bearing three contiguous stereogenic centers in good yields, excellent enantiomeric excesses, and up to high diastereomeric ratios.

SUBMITTER: Blumel M

PROVIDER: S-EPMC4611353 | biostudies-literature | 2014 Nov

REPOSITORIES: biostudies-literature

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Asymmetric synthesis of tetrahydropyridines via an organocatalytic one-pot multicomponent Michael/aza-Henry/cyclization triple domino reaction.

Blümel Marcus M Chauhan Pankaj P Hahn Robert R Raabe Gerhard G Enders Dieter D

Organic letters 20141107 22

A low loading of a quinine-derived squaramide efficiently catalyzes the triple-domino Michael/aza-Henry/cyclization reaction between 1,3-dicarbonyl compounds, β-nitroolefins, and aldimines to provide tetrahydropyridines bearing three contiguous stereogenic centers in good yields, excellent enantiomeric excesses, and up to high diastereomeric ratios. ...[more]

PMID: 25379786

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