Blackwell, J. Henry published the artcileVisible-Light-Mediated Carbonyl Alkylative Amination to All-Alkyl 伪-Tertiary Amino Acid Derivatives, Name: tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, the publication is Journal of the American Chemical Society (2021), 143(3), 1598-1609, database is CAplus and MEDLINE.
The all-alkyl 伪-tertiary amino acid scaffold represents an important structural feature in many biol. and pharmaceutically relevant mols. Syntheses of this class of mol., however, often involve multiple steps and require activating auxiliary groups on the nitrogen atom or tailored building blocks. A straightforward, single-step, and modular methodol. for the synthesis of all-alkyl 伪-tertiary amino esters was reported. This new strategy uses visible light and a silane reductant to bring about a carbonyl alkylative amination reaction that combines a wide range of primary amines, 伪-ketoesters, and alkyl iodides to form functionally diverse all-alkyl 伪-tertiary amino esters. Bronsted acid-mediated in situ condensation of primary amine and 伪-ketoester delivers the corresponding ketiminium species, which undergoes rapid 1,2-addition of an alkyl radical (generated from an alkyl iodide by the action of visible light and silane reductant) to form an aminium radical cation. Upon a polarity-matched and irreversible hydrogen atom transfer from electron rich silane, the electrophilic aminium radical cation is converted to an all-alkyl 伪-tertiary amino ester product. The benign nature of this process allows for broad scope in all three components and generates structurally and functionally diverse suite of 伪-tertiary amino esters that will likely have widespread use in academic and industrial settings.
Journal of the American Chemical Society published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Name: tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate.
Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles