Alkene Syn- and Anti-Oxyamination with Malonoyl Peroxides

Jonathan M Curle; Marina C Perieteanu; Philip G Humphreys; Alan R Kennedy; Nicholas C O Tomkinson

doi:10.1021/acs.orglett.0c00253

Alkene Syn- and Anti-Oxyamination with Malonoyl Peroxides

Org Lett. 2020 Feb 21;22(4):1659-1664. doi: 10.1021/acs.orglett.0c00253. Epub 2020 Jan 30.

Authors

Jonathan M Curle¹, Marina C Perieteanu¹, Philip G Humphreys², Alan R Kennedy¹, Nicholas C O Tomkinson¹

Affiliations

¹ Department of Pure and Applied Chemistry, WestCHEM, Thomas Graham Building , University of Strathclyde , 295 Cathedral Street , Glasgow G1 1XL , U.K.
² GlaxoSmithKline Medicines Research Centre , Gunnels Wood Road , Stevenage SG1 2NY , U.K.

Abstract

Malonoyl peroxide 6 is an effective reagent for the syn- or anti-oxyamination of alkenes. Reaction of 6 and an alkene in the presence of O-tert-butyl-N-tosylcarbamate (R³ = CO₂^tBu) leads to the anti-oxyaminated product in up to 99% yield. Use of O-methyl-N-tosyl carbamate (R³ = CO₂Me) as the nitrogen nucleophile followed by treatment of the product with trifluoroacetic acid leads to the syn-oxyaminated product in up to 77% yield. Mechanisms consistent with the observed selectivities are proposed.

Publication types

Research Support, Non-U.S. Gov't