Diastereomeric Fluoroolefins as Peptide Bond Mimics Prepared by Asymmetric Reductive Amination of α‐Fluoroenones | Zendy

Dutheuil Guillaume | Zendy; CouveBonnaire Samuel | Zendy; Pannecoucke Xavier | Zendy

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Diastereomeric Fluoroolefins as Peptide Bond Mimics Prepared by Asymmetric Reductive Amination of α‐Fluoroenones

Author(s) -

Dutheuil Guillaume,

CouveBonnaire Samuel,

Pannecoucke Xavier

Publication year - 2007

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200604246

Subject(s) - reductive amination , diastereomer , imine , stereoselectivity , dipeptide , chemistry , combinatorial chemistry , amination , stereochemistry , organic chemistry , peptide , catalysis , biochemistry

Fluoropeptidomimetics : An efficient asymmetric reductive amination of fluoroenones has been developed that affords potential precursors of fluoropeptide isosteres. Stereoselective routes with different reductive agents provided both diastereomers from the same nonracemic sulfinyl imine. The method was applied to the synthesis of different dipeptide analogues.

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