ArticleChemical science2017
Catalyst-controlled regioselectivity in phosphine catalysis: the synthesis of spirocyclic benzofuranones
Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Origin of Substituent-Modulated Regioselectivity in Phosphine-Catalyzed [3 + 2] Cyclization of Allenoates and Enones: A Kinetic Shift toward Curtin-Hammett Control.The Journal of organic chemistry · 2025Article
- Solvent-Controlled Regiodivergent Friedel-Crafts Reactions of 1-Naphthol with In Situ Generated Aza-The Journal of organic chemistry · 2025Article
- Switchable Synthesis of Tritylone Alcohols and 2-Benzoylbenzoate Esters from Spiroindane-1,3-diones.The Journal of organic chemistry · 2024Article
- Phosphine-catalyzed divergent domino processes between γ-substituted allenoates and carbonyl-activated alkenes.Chemical science · 2022Article
- Phosphine Organocatalysis.Chemical reviews · 2018Review
- Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones withChemical science · 2018Article
Corrections and comments
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Authors and funding
6 authors.
Funding
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Abstract
Catalyst-controlled regiodivergent [3 + 2] annulations of aurones and allenoates have been developed. When a dipeptide phosphine catalyst with an l-d- configuration was employed, α-selective [3 + 2] annulation products could be obtained with good regioselectivities and enantioselectivities. With the employment of l-l- dipeptide phosphines, γ-selective annulation products could be selectively obtained with excellent enantioselectivities. By simply tuning the catalyst configurations, a wide range of α-selective or γ-selective spirocyclic benzofuranones with either aryl or alkyl substitutions could be readily prepared. DFT calculations suggest that the conformation of the dipeptide phosphines influences the hydrogen bonding interactions or the distortion energy, resulting in delicate energy differentiation in the transition states, and accounting for the observed regioselectivity.
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Registered trials
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