Alkene syn- and anti-oxyamination with malonoyl peroxides

Research output: Contribution to journalArticle

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 = CO2tBu) 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.
Original languageEnglish
Number of pages6
JournalOrganic Letters
Early online date30 Jan 2020
DOIs
Publication statusE-pub ahead of print - 30 Jan 2020

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Peroxides
Alkenes
peroxides
alkenes
Trifluoroacetic Acid
Nucleophiles
Carbamates
products
Nitrogen
nucleophiles
reagents
selectivity
nitrogen
acids

Keywords

  • organic chemistry
  • Malonoyl peroxide
  • alkenes
  • alkene oxyamination

Cite this

@article{66ba47adf2ee4fa987a3c58da498e0e8,
title = "Alkene syn- and anti-oxyamination with malonoyl peroxides",
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 = CO2tBu) 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.",
keywords = "organic chemistry, Malonoyl peroxide, alkenes, alkene oxyamination",
author = "Curle, {Jonathan M.} and Perieteanu, {Marina C.} and Humphreys, {Philip G.} and Kennedy, {Alan R.} and Tomkinson, {Nick C. O.}",
year = "2020",
month = "1",
day = "30",
doi = "10.1021/acs.orglett.0c00253",
language = "English",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",

}

TY - JOUR

T1 - Alkene syn- and anti-oxyamination with malonoyl peroxides

AU - Curle, Jonathan M.

AU - Perieteanu, Marina C.

AU - Humphreys, Philip G.

AU - Kennedy, Alan R.

AU - Tomkinson, Nick C. O.

PY - 2020/1/30

Y1 - 2020/1/30

N2 - 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 = CO2tBu) 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.

AB - 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 = CO2tBu) 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.

KW - organic chemistry

KW - Malonoyl peroxide

KW - alkenes

KW - alkene oxyamination

U2 - 10.1021/acs.orglett.0c00253

DO - 10.1021/acs.orglett.0c00253

M3 - Article

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

ER -