Amino acids and catalytic preparatory methods

2The invention provides novel compounds and methods to carry out organocatalytic Michael additions of aldehydes to nitroethylene catalyzed by a proline derivative to provide α-substituted-γ-nitroaldehydes. The reaction can be rendered enantioselective when a chiral pyrrolidine catalyst is used, allo...

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Bibliographic Details
Main Authors Gellman, Samuel Helmer, Chi, Yonggui, Guo, Li
Format Patent
LanguageEnglish
Published 18.09.2012
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Summary:2The invention provides novel compounds and methods to carry out organocatalytic Michael additions of aldehydes to nitroethylene catalyzed by a proline derivative to provide α-substituted-γ-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 γ-amino acids, which are essential for systematic conformational studies of γ-peptide foldamers.