Cristin-resultat-ID: 1416746
Sist endret: 22. mars 2018, 16:20
NVI-rapporteringsår: 2017
Resultat
Vitenskapelig artikkel
2017

Rearrangement reactions leading to optically active α,α-disubstituted primary allylamines

Bidragsytere:
  • Martin Hennum
  • Hege Hortemo Odden og
  • Lise-Lotte Gundersen

Tidsskrift

European Journal of Organic Chemistry
ISSN 1434-193X
e-ISSN 1099-0690
NVI-nivå 1

Om resultatet

Vitenskapelig artikkel
Publiseringsår: 2017
Volum: 2017
Hefte: 4
Sider: 846 - 860

Importkilder

Scopus-ID: 2-s2.0-85011659395

Beskrivelse Beskrivelse

Tittel

Rearrangement reactions leading to optically active α,α-disubstituted primary allylamines

Sammendrag

Synthetic routes to α,α-disubstituted allylamines have been examined. Racemic compounds were conveniently prepared by thermal Overman rearrangements of primary allyl alcohols with trisubstituted double bonds, but rearrangement of these substrates by the only commercially available compound known to catalyze enantioselective Overman rearrangements, the cobalt oxazoline palladacycle (R)-COP-Cl, failed. Instead optically active secondary allyl alcohols with trisubstituted double bonds, obtained by CBS-mediated reduction of the corresponding methyl ketones, were synthesized and converted to α,α-disubstituted allylamines via a thermal Overman rearrangement or an allyl cyanate to isocyanate rearrangement. High chiral transfer (90-99%) was obtained with both reaction sequences, but the chemical yields were greatly improved when the allyl cyanate to isocyanate rearrangement were employed.

Bidragsytere

Martin Hennum

  • Tilknyttet:
    Forfatter
    ved Kjemisk institutt ved Universitetet i Oslo

Hege Hortemo Odden

  • Tilknyttet:
    Forfatter
    ved Kjemisk institutt ved Universitetet i Oslo

Lise-Lotte Gundersen

  • Tilknyttet:
    Forfatter
    ved Kjemisk institutt ved Universitetet i Oslo
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