Aza-Rubottom Oxidation: Synthetic Access to Primary α-Aminoketones

Zhe Zhou; Qing-Qing Cheng; László Kürti

doi:10.1021/jacs.8b13818

Aza-Rubottom Oxidation: Synthetic Access to Primary α-Aminoketones

J Am Chem Soc. 2019 Feb 13;141(6):2242-2246. doi: 10.1021/jacs.8b13818. Epub 2019 Feb 1.

Authors

Zhe Zhou¹, Qing-Qing Cheng¹, László Kürti¹

Affiliation

¹ Department of Chemistry , Rice University BioScience Research Collaborative , 6500 Main Street , Houston , Texas 77030 , United States.

Abstract

An aza analogue of the Rubottom oxidation is reported. This facile transformation takes place at ambient temperature and directly converts silyl enol ethers to the corresponding primary α-aminoketones. The use of hexafluoroisopropanol (HFIP) as the solvent is essential for the success of this reaction. Overall this process is well-suited for the aza-functionalization and derivatization of complex organic molecules.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Aza Compounds / chemistry*
Catalysis
Ketones / chemical synthesis*
Ketones / chemistry*
Oxidation-Reduction
Stereoisomerism

Substances

Aza Compounds
Ketones

Grants and funding

R01 GM114609/GM/NIGMS NIH HHS/United States