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Synthesis of trans-3-substituted cyclohexylamines via Brønsted acid catalyzed and substrate-mediated triple organocatalytic cascade reaction

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Zhou,  Jian
Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Zhou, J., & List, B. (2007). Synthesis of trans-3-substituted cyclohexylamines via Brønsted acid catalyzed and substrate-mediated triple organocatalytic cascade reaction. Synlett, (13), 2037-2040. doi:10.1055/s-2007-984877.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-914F-F
Abstract
We report a new organocatalytic cascade reaction. A combination of the amine substrate with a catalytic amount of a Brønsted acid merges enamine and iminium catalysis with Brønsted acid catalysis in a new organocatalytic cascade reaction. We found that the aniline substrate itself in combination with a catalytic amount of PTSA·H2O can function as an aminocatalyst accomplishing an aldol condensation-conjugate reduction cascade, which ­terminates in a Brønsted acid catalyzed reductive amination incorporating the amine substrate into the final product. This transformation furnishes trans-3-substituted cyclohexyl amines in good yields and good diastereoselectivities.