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Communication

Organocatalytic Asymmetric Reaction Cascade to Substituted Cyclohexylamines

Supporting Info

Jian Zhou and Benjamin List*

Max-Planck-Institut fr Kohlenforschung, D-45470 Mlheim an der Ruhr, Germany

J. Am. Chem. Soc., 2007, 129 (24), pp 7498–7499

DOI: 10.1021/ja072134j

Publication Date (Web): May 27, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, list@mpi-muelheim.mpg.de

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.

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Published In Issue June 20, 2007
Received March 27, 2007

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Communication

Organocatalytic Asymmetric Reaction Cascade to Substituted Cyclohexylamines

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Double Bond Isomerization/Enantioselective Aza-Petasis−Ferrier Rearrangement Sequence as an Efficient Entry to Anti- and Enantioenriched β-Amino Aldehydes

Highly Enantioselective Transfer Hydrogenation of α,β-Unsaturated Ketones Highly Enantioselective Transfer Hydrogenation of α,β-Unsaturated Ketones

Enantioselective Organocatalytic Reductive Amination

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