Asymmetric Synthesis of Tetrahydropyridines via an Organocatalytic One-Pot Multicomponent Michael/Aza-Henry/Cyclization Triple Domino Reaction | Zendy

Marcus Blümel | Zendy; Pankaj Chauhan | Zendy; Robert G. Hahn | Zendy; Gerhard Raabe | Zendy; Dieter Enders | Zendy

Open Access

Asymmetric Synthesis of Tetrahydropyridines via an Organocatalytic One-Pot Multicomponent Michael/Aza-Henry/Cyclization Triple Domino Reaction

Author(s) -

Marcus Blümel,

Pankaj Chauhan,

Robert G. Hahn,

Gerhard Raabe,

Dieter Enders

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol503024d

Subject(s) - squaramide , stereocenter , michael reaction , chemistry , domino , diastereomer , cascade reaction , nitroaldol reaction , cinchona , organocatalysis , enantiomer , aldimine , enantioselective synthesis , organic chemistry , stereochemistry , catalysis

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.

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