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Synthesis 2019; 51(23): 4348-4358
DOI: 10.1055/s-0037-1610732
DOI: 10.1055/s-0037-1610732
feature
Catalyst-Free [2,3]-Sigmatropic Rearrangement Reactions of Photochemically Generated Ammonium Ylides
Funded by the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) – project no. 408033718.Further Information
Publication History
Received: 13 July 2019
Accepted after revision: 06 September 2019
Publication Date:
14 October 2019 (online)
Abstract
The rearrangement reaction of ammonium ylides furnishes valuable α,α-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).
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610732.
- Supporting Information
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Selected references on [1,2]-sigmatropic rearrangement reactions of ylides:
Selected references on [2,3]-sigmatropic rearrangement reactions of light chalcogenonium ylides:
Selected references on [2,3]-sigmatropic rearrangement reactions of selenonium ylides:
Selected references on sigmatropic rearrangement reactions of halonium ylides:
Selected references on dealkylative rearrangement reactions:
Selected references on sigmatropic rearrangement reactions of ammonium ylides:
References on [2,3]-sigmatropic rearrangement reactions of ammonium ylides:
References on sigmatropic rearrangement of ammonium ylides with donor–acceptor diazoalkanes:
Selected references:
Selected articles on nonprecious metal-catalyzed carbene-transfer reactions:
Selected references: