2012
DOI: 10.1055/s-0031-1290598
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Investigation of Additive Effects in Enantioselective Copper-Catalysed C-H Insertion and Aromatic Addition Reactions of α-Diazocarbonyl Compounds

Abstract: Significant enhancements in enantioselectivities and reaction efficiencies in asymmetric copper-catalysed C-H insertion and aromatic addition reactions of a-diazocarbonyl compounds in the presence of various group I salts are reported. For the first time in carbenoid chemistry, evidence for the critical role of the metal cation is described.

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Cited by 18 publications
(1 citation statement)
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“…[34][35][36] The copper catalyst system, comprising of copper-bis(oxazoline) ligand-NaBARF, has been demonstrated by the Maguire group to effect C-H insertion reactions with very high levels of enantiocontrol across a diverse range of α-diazocarbonyl substrates leading to tetrahydrothiopyrans-S,S-dioxides, sulfolanes, cyclopentanones, β-and γlactams (Scheme 2, A). [34][35][36][37][38][39][40] Of particular interest to this study were the reactions conducted in our team by Flynn 34 and later expanded upon by Shiely 36 concerning the copper-bis(oxazoline) catalysed asymmetric transformations of α-diazo-β-keto sulfones to tetrahydrothiopyrans-S,S-dioxides (up to 98% ee, Scheme 2, A).…”
Section: Scheme 1 Previous Work By Mckerveymentioning
confidence: 99%
“…[34][35][36] The copper catalyst system, comprising of copper-bis(oxazoline) ligand-NaBARF, has been demonstrated by the Maguire group to effect C-H insertion reactions with very high levels of enantiocontrol across a diverse range of α-diazocarbonyl substrates leading to tetrahydrothiopyrans-S,S-dioxides, sulfolanes, cyclopentanones, β-and γlactams (Scheme 2, A). [34][35][36][37][38][39][40] Of particular interest to this study were the reactions conducted in our team by Flynn 34 and later expanded upon by Shiely 36 concerning the copper-bis(oxazoline) catalysed asymmetric transformations of α-diazo-β-keto sulfones to tetrahydrothiopyrans-S,S-dioxides (up to 98% ee, Scheme 2, A).…”
Section: Scheme 1 Previous Work By Mckerveymentioning
confidence: 99%