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Stereoselective metal-free synthesis of β-amino thioesters with tertiary and quaternary stereogenic centers.

Angewandte Chemie (International ed. in English) (2014-03-20)
Annette Bahlinger, Sven P Fritz, Helma Wennemers
ABSTRACT

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 β(2)- and β(2,3,3)-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 β(2,3)-frameworks. In addition, the value of the β-amino thioesters was shown in coupling-reagent-free peptide synthesis.

MATERIALS
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