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Issue 38, 2015
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Asymmetric palladium-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant

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Abstract

Palladium/chiral diphosphine-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a terminal reductant affords cis-disubstituted pyrrolidine, tetrahydrofuran, and spiro carbocycle in high enantioselectivity. The formate does not cause allylpalladium reduction under the catalysis. The highly stereoselective cyclization would proceed through a cationic η1-allylpalladium ligated by diphosphine.

Graphical abstract: Asymmetric palladium-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant

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Publication details

The article was received on 14 Mar 2015, accepted on 02 Apr 2015 and first published on 03 Apr 2015


Article type: Communication
DOI: 10.1039/C5CC02176F
Chem. Commun., 2015,51, 8027-8030

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    Asymmetric palladium-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant

    H. Tsukamoto, A. Kawase and T. Doi, Chem. Commun., 2015, 51, 8027
    DOI: 10.1039/C5CC02176F

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