1022985-40-5Relevant academic research and scientific papers
Amino acids and catalytic preparatory methods
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Page/Page column 11, (2009/10/30)
The 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 γ2-amino acids, which are essential for systematic conformational studies of γ-peptide foldamers.
Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: Efficient access to γ2-amino acids
Chi, Yonggui,Guo, Li,Kopf, Nathan A.,Gellman, Samuel H.
, p. 5608 - 5609 (2008/12/22)
Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene catalyzed by (S)-diphenylprolinol silyl ether provides β-substituted-δ-nitroalcohols in nearly optically pure form (96-99% ee). The Michael adducts bear a single substituent adjacent to the carbonyl and can be efficiently converted to protected γ2-amino acids, which are essential for the systematic conformational studies of γ-peptide foldamers. Copyright
