Chiral aldehyde catalysis for the catalytic asymmetric activation of glycine esters.

08:00 EDT 11th July 2018 | BioPortfolio

Summary of "Chiral aldehyde catalysis for the catalytic asymmetric activation of glycine esters."

Chiral aldehyde catalysis is uniquely suitable for the direct asymmetric α-functionalization of N-unprotected amino acids, because aldehydes can reversibly form imines. However, there have been few successful reports of these transformations. In fact, only chiral aldehyde catalyzed aldol reactions of amino acids and alkylation of 2-amino malonates have been reported with good chiral induction. Here, we report a novel type of chiral aldehyde catalyst based on face control of the enolate intermediates. The resulting chiral aldehyde is the first efficient non-pyridoxal-dependent catalyst that can promote the direct asymmetric α-functionalization of N-unprotected glycine esters. Possible transition states and the proton transfer process were investigated by density functional theory calculations.


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This article was published in the following journal.

Name: Journal of the American Chemical Society
ISSN: 1520-5126


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