Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 14, Pages 2764-2778Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob00025c
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This review surveys recent synergistic applications of combining chiral organocatalysts with achiral metals for stereoselective transformations. The transformations are classified based on reactivity modes, focusing on organocatalytic activation of carbonyl substrates as chiral nucleophiles and electrophiles in combination with achiral metal co-catalysts. Radical reactions mediated by achiral metal complexes via photocatalysis are also presented, revealing privileged structures and highlighting opportunities for further development in this exciting field.
In this review we survey recent synergistic applications of a chiral organocatalyst with an achiral metal to perform stereoselective transformations of synthetic utility (since 2016). The transformations are classified by the modes of reactivity deployed, focussing on organocatalytic activation of carbonyl substrates as chiral nucleophiles via the alpha-position (e.g., as enamines) and as chiral electrophiles via the beta-position (e.g., as iminium ions) combined with complementary activation of their reaction partners by an achiral metal co-catalyst (e.g., Pd or Cu-based). Corresponding radical reactions are also presented in which photocatalysis mediated by achiral metal complexes replaces the metal co-catalyst. Certain privileged structures are revealed and opportunities to develop this exciting field are highlighted.
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