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Issue 10, 2017
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Pd-catalyzed asymmetric allylic alkylations via C–H activation of N-allyl imines with glycinates

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Abstract

Herein is reported the first example of palladium-catalyzed asymmetric allylic alkylation (AAA) reactions involving 2-aza-π-allyl palladium intermediates. The 2-aza-π-allyl complex was generated via a novel mode of activation of N-allyl imines. Pd-catalyzed C(sp3)–H activation of N-allyl imines and subsequent nucleophilic attack by glycinates delivered vicinal diamino derivatives as the sole regioisomers with high levels of diastereo- and enantio-control in the presence of the chiral, bidentate (S,S)-Cy-DIOP ligand. This procedure is highly atom economical and could also be performed by a simple one-pot operation starting from aldehydes, allyl amines and glycinates under mild conditions. The products of this transformation could be converted into various useful derivatives, where the allyl substitution serves as a unique tool for differentiating the two amino moieties in the products.

Graphical abstract: Pd-catalyzed asymmetric allylic alkylations via C–H activation of N-allyl imines with glycinates

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Publication details

The article was received on 30 Jun 2017, accepted on 15 Aug 2017 and first published on 15 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC02899G
Citation: Chem. Sci., 2017,8, 6815-6821
  • Open access: Creative Commons BY-NC license
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    Pd-catalyzed asymmetric allylic alkylations via C–H activation of N-allyl imines with glycinates

    B. M. Trost and X. Li, Chem. Sci., 2017, 8, 6815
    DOI: 10.1039/C7SC02899G

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