Premium
Stereoselective Metal‐Free Synthesis of β‐Amino Thioesters with Tertiary and Quaternary Stereogenic Centers
Author(s) -
Bahlinger Annette,
Fritz Sven P.,
Wennemers Helma
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201310532
Subject(s) - stereocenter , stereoselectivity , decarboxylation , chemistry , reagent , amino acid , combinatorial chemistry , stereochemistry , mannich reaction , organic chemistry , enantioselective synthesis , catalysis , biochemistry
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.