Organocatalytic Asymmetric Reaction Cascade to Substituted Cyclohexylamines

Zhou, Jian; List, Benjamin

doi:10.1021/ja072134j

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Organocatalytic Asymmetric Reaction Cascade to Substituted Cyclohexylamines

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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). Organocatalytic Asymmetric Reaction Cascade to Substituted Cyclohexylamines. Journal of the American Chemical Society, 129(24), 7498-7499. doi:10.1021/ja072134j.

Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-9175-8

Abstract

We report a new strategy for organocatalytic cascade reactions. Accordingly, enamine catalysis, iminium catalysis, and Brønsted acid catalysis can work in concert in a highly enantioselective organocatalytic cascade sequence toward chiral cis-3-substituted cyclohexylamines. We found that an achiral amine in combination with a catalytic amount of a chiral Brønsted acid can accomplish an aldol addition−dehydration−conjugate reduction−reductive amination to provide potential intermediates of pharmaceutically active compounds in good yields and excellent enantioselectivities.