An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.
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Aerobic oxynitration of alkynes with (t)BuONO and TEMPO.
Org Lett
December 2014
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.
View Article and Find Full Text PDFMultifunctionalization of alkenes via aerobic oxynitration and sp3 C-H oxidation.
Chem Commun (Camb)
March 2013
School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
A method for direct functionalization of three positions including an unactivated C-H bond of aliphatic alkenes using tert-butyl nitrite and molecular oxygen to give γ-lactols has been developed. The present reaction proceeds through a sequence of radical processes involving oxynitration followed by aerobic oxidation of an sp(3) C-H bond. This multifunctionalization reaction requires neither metallic reagents nor photolysis and proceeds under mild conditions.
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