Methods for preparing amides and amino acids

The invention provides novel compounds and methods to carry out organocatalytic Michael additions of aldehydes to nitroethylene catalyzed by a proline derivative to provide alpha-substituted-gamma-nitroaldehydes. The reaction can be rendered enantioselective when a chiral pyrrolidine catalyst is use...

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Bibliographic Details
Main Authors GELLMAN SAMUEL HELMER, CHI YONGGUI, GUO LI
Format Patent
LanguageEnglish
Published 28.01.2014
Subjects
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
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Summary:The invention provides novel compounds and methods to carry out organocatalytic Michael additions of aldehydes to nitroethylene catalyzed by a proline derivative to provide alpha-substituted-gamma-nitroaldehydes. The reaction can be rendered enantioselective when a chiral pyrrolidine catalyst is used, allowing for Michael adducts in nearly optically pure form (e.g., 96-99% e.e.). The Michael adducts can bear a single substituent or dual substituents adjacent to the carbonyl. The Michael adducts can be efficiently converted to protected gamma2-amino acids, which are essential for systematic conformational studies of gamma-peptide foldamers.
Bibliography:Application Number: US201213621553