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Organocatalytic Asymmetric Reaction Cascade to Substituted Cyclohexylamines

Jian Zhou and Benjamin List*

*Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim an der Ruhr, Germany, Email:

J. Zhou, B. List, J. Am. Chem. Soc., 2007, 129, 7498-7499.

DOI: 10.1021/ja072134j (free Supporting Information)


An achiral amine in combination with a catalytic amount of a chiral Brønsted acid can accomplish an aldol addition-dehydration-conjugate reduction-reductive amination with 2,6-diketones to provide cyclohexylamines as potential intermediates of pharmaceutically active compounds in good yields and excellent enantioselectivities.

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proposed reaction pathway

Key Words

aldol condensation, reductive amination, organocatalysis, Hantzsch Ester

ID: J48-Y2007-1970