Application In Synthesis of 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 1,2,3,4-Tetrahydroquinoline-3-carboxylic acid, is researched, Molecular C10H11NO2, CAS is 114527-53-6, about Traceless Electrophilic Amination for the Synthesis of Unprotected Cyclic β-Amino Acids. Author is Yu, Jin-Sheng; Espinosa, Miguel; Noda, Hidetoshi; Shibasaki, Masakatsu.
Electrophilic aminations involve an umpolung of a nitrogen atom, providing an alternate, distinctive synthetic strategy. The recent advent of various designed O-substituted hydroxylamines has significantly advanced this research field. An underappreciated issue is atom economy of the transformations: The necessary activating group on the oxygen atom is left in coproduced waste. Herein, the authors describe Rh-catalyzed electrophilic amination of substituted isoxazolidin-5-ones for the synthesis of unprotected, cyclic β-amino acids featuring either benzo-fused or spirocyclic scaffolds. Using the cyclic hydroxylamines allows for retaining both nitrogen and oxygen functionalities in the product. The traceless, redox neutral process proceeds on a gram scale with as little as 0.1 mol % catalyst loading. In contrast to related electrophilic aminations in the literature, a series of mechanistic experiments suggests a unique pathway involving spirocyclization, followed by the skeletal rearrangement. The insights provided herein shed light on a nuanced reactivity of the active species, Rh-nitrenoid generated from the activated hydroxylamine, and extend the knowledge on electrophilic aromatic substitutions.
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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com