4.5 Article

Catalyst-Free [2,3]-Sigmatropic Rearrangement Reactions of Photochemically Generated Ammonium Ylides

Journal

SYNTHESIS-STUTTGART
Volume 51, Issue 23, Pages 4348-4358

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1610732

Keywords

photochemistry; diazoalkanes; carbenes; amines; ylides; rearrangement

Funding

  1. Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) [408033718]

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The rearrangement reaction of ammonium ylides furnishes valuable alpha,alpha-disubstituted amino esters. In this work, we describe the visible-light photolysis reaction of aryldiazoacetates in the presence of tertiary amines that react via a free ammonium ylide in a sigmatropic rearrangement reaction to provide amino esters in moderate to very good yields (33 examples, up to 97% yield).

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