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  Synthesis of trans-3-Substituted Cyclohexylamines via Brønsted Acid Cata­lyzed and Substrate-Mediated Triple Organocatalytic Cascade Reaction

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.

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 Creators:
Zhou, Jian1, Author              
List, Benjamin2, Author              
Affiliations:
1Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445589              
2Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: organocatalytic cascade reaction; substrate co-catalyzed; 3-substituted cyclohexyl amine; organocatalysis
 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.

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Language(s): eng - English
 Dates: 2007-05-172007-07-122007-08-01
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1055/s-2007-984877
 Degree: -

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Title: Synlett
  Abbreviation : Synlett
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Stuttgart : Georg Thieme Verlag
Pages: - Volume / Issue: (13) Sequence Number: - Start / End Page: 2037 - 2040 Identifier: ISSN: 0936-5214
CoNE: https://pure.mpg.de/cone/journals/resource/954925570856