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.
Highlights
Catalytic asymmetric C(sp3)–H bond functionalization is an emerging synthetic method affording direct access to useful chiral building blocks from stable organic molecules.[1]
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
Catalytic asymmetric allylation of aldehydes using unactivated alkenes as pronucleophiles produces enantiomerically-enriched homoallylic alcohols, which act as versatile synthetic intermediates for numerous functional molecules, including various drug leads.[2]
Summary
Catalytic asymmetric C(sp3)–H bond functionalization is an emerging synthetic method affording direct access to useful chiral building blocks from stable organic molecules.[1]. ISSN 2041-6539 EDGE ARTICLE Harunobu Mitsunuma, Motomu Kanai et al 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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