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- W4224223180 abstract "Abstract Enantioselective catalytic formation of polyfunctional molecules, such as non‐natural amino acids, is important for the efficient production of many chiral compounds. To this end, we present here the synthesis and evaluation of the catalytic activity of bifunctional peptide–thiourea organocatalysts. These hybrid organocatalysts consist of Pro‐Pro dipeptide and thiourea moiety connected via a 1,2‐diaminocyclohexane unit. These catalysts promoted challenging Mannich reaction between α‐imino esters and pyruvates, providing orthogonally protected oxo‐glutamate derivatives. The N ‐ tosyl‐protected imino ester, as the most active imine, was required to compensate for the poor reactivity of pyruvates. DFT calculations, NMR, and CD spectroscopy help elucidate the mode of action of these catalysts. Configuration of the dipeptide Pro‐Pro moiety is responsible for the sense of the stereoinduction of the Mannich reaction." @default.
- W4224223180 created "2022-04-26" @default.
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- W4224223180 date "2022-05-12" @default.
- W4224223180 modified "2023-09-27" @default.
- W4224223180 title "Pro‐Pro Dipeptide‐Thiourea Organocatalyst in the Mannich Reaction between α‐Imino Esters and Pyruvates" @default.
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- W4224223180 doi "https://doi.org/10.1002/ejoc.202200106" @default.
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