1603833-15-3Relevant academic research and scientific papers
Stereoselective metal-free synthesis of β-amino thioesters with tertiary and quaternary stereogenic centers
Bahlinger, Annette,Fritz, Sven P.,Wennemers, Helma
, p. 8779 - 8783 (2014)
β-Amino thioesters are important natural building blocks for the synthesis of numerous bioactive molecules. An organocatalyzed Mannich reaction was developed which provides direct and highly stereoselective access to acyclic β2- and β2,3,3-amino thioesters with adjacent tertiary and quaternary stereocenters. Mechanistic studies showed that the stereochemical course of the reaction can be controlled by the choice of the substrates. The β-amino thioesters were further functionalized by, for example, stereoselective decarboxylation to access β2,3- frameworks. In addition, the value of the β-amino thioesters was shown in coupling-reagent-free peptide synthesis.
