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Issue 12, 2019
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Catalytic asymmetric allylation of aldehydes with alkenes through allylic C(sp3)–H functionalization mediated by organophotoredox and chiral chromium hybrid catalysis

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Abstract

We describe a hybrid system that realizes cooperativity between an organophotoredox acridinium catalyst and a chiral chromium complex catalyst, thereby enabling unprecedented exploitation of unactivated hydrocarbon alkenes as precursors to chiral allylchromium nucleophiles for asymmetric allylation of aldehydes. The reaction proceeds under visible light irradiation at room temperature, affording the corresponding homoallylic alcohols with a diastereomeric ratio >20/1 and up to 99% ee. The addition of Mg(ClO4)2 markedly enhanced both the reactivity and enantioselectivity.

Graphical abstract: Catalytic asymmetric allylation of aldehydes with alkenes through allylic C(sp3)–H functionalization mediated by organophotoredox and chiral chromium hybrid catalysis

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Publication details

The article was received on 19 Dec 2018, accepted on 16 Jan 2019 and first published on 17 Jan 2019


Article type: Edge Article
DOI: 10.1039/C8SC05677C
Citation: Chem. Sci., 2019,10, 3459-3465
  • Open access: Creative Commons BY license
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    Catalytic asymmetric allylation of aldehydes with alkenes through allylic C(sp3)–H functionalization mediated by organophotoredox and chiral chromium hybrid catalysis

    H. Mitsunuma, S. Tanabe, H. Fuse, K. Ohkubo and M. Kanai, Chem. Sci., 2019, 10, 3459
    DOI: 10.1039/C8SC05677C

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