Organocatalytic Enantioselective Mukaiyama-Mannich Reaction of Isatin-Derived Ketimines for the Synthesis of Oxindolyl-β3,3-Amino Acid Esters.

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ID: 34665
2019
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Ranked #84 of 117 articles by views in Chemistry (Weinheim an der Bergstrasse, Germany)

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Abstract
Mukaiyama-Mannich reactions of ester enolate equivalents with aldimines have elegantly been used for the asymmetric synthesis of β-amino acids; nevertheless, the corresponding asymmetric reaction employing ketimines are until unexplored. Herein, we disclose the first organocatalytic enantioselective Mukaiyama-Mannich reaction employing isatin-derived ketimines with unsubstituted silyl ketene acetals towards the scalable synthesis of 2-oxoindolinyl-β3,3-amino acid esters at room temperature with excellent enantioselectivities (ee >99.5%). Ultra-low catalyst loading (as low as 250 ppm) could be used for the quantitative product formation with high enantiopurity. The synthetic utility of this protocol has been showcased in the short step formal synthesis of pharmaceutically demanding (+)-AG-041R, a potent gastrin/CCK-B receptor antagonist.
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hajra2019organocatalyticchemistry Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Hajra, Saumen;Laskar, Sujay;Jana, Bibekananda;
Journal Chemistry (Weinheim an der Bergstrasse, Germany)
Year 2019
DOI
10.1002/chem.201903512
URL
Keywords Keywords not found

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