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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: http://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.