Abstract
AbstractThe effect of β3‐amino acids on the conformation and catalytic performance of the peptidic catalyst H‐dPro‐Pro‐Glu‐NH2 was investigated. Analogues of the peptidic catalyst bearing instead of the α‐amino acids the respective β3‐amino acids were prepared and their reactivity and stereoselectivity was investigated in conjugate addition reactions of aldehydes to nitroolefins. Additional computational studies provided insights into the preferred conformations of the peptidic catalysts. The results show that conformational flexibility at the N‐terminus has a severe effect on the stereoselectivity but is tolerated at the C‐terminus.
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