2022
DOI: 10.1039/d1sc06364b
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Phosphine-catalyzed divergent domino processes between γ-substituted allenoates and carbonyl-activated alkenes

Abstract: Highly enantioselective and chemodivergent domino reactions between g-substituted allenoates and activated alkenes have been developed. In the presence of NUSIOC-Phos, triketone enone substrates smoothly reacted with γ-substituted allenoates to form...

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Cited by 19 publications
(4 citation statements)
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“…First, 1 was dissolved in THF and hydrolyzed by HCl solution. The crude product was further purified by silica gel CC to obtain pure products 3 and 4 [ 29 ]. Then, 1 was dissolved in THF and H 2 O, the hydrolysis condition was changed to alkaline KOH solution, and the reaction was at 0 °C for 2 h to prepare the pure product 5 .…”
Section: Resultsmentioning
confidence: 99%
“…First, 1 was dissolved in THF and hydrolyzed by HCl solution. The crude product was further purified by silica gel CC to obtain pure products 3 and 4 [ 29 ]. Then, 1 was dissolved in THF and H 2 O, the hydrolysis condition was changed to alkaline KOH solution, and the reaction was at 0 °C for 2 h to prepare the pure product 5 .…”
Section: Resultsmentioning
confidence: 99%
“…In 2022, Lu and co-workers developed a phosphinecatalysed chemodivergent domino reaction using γ-substituted allenoates 100 and activated alkenes (Scheme 32a). [74] The allenoates have provided the bicyclic furofurans 138 upon reaction with triketone enone 137 under NUSIOC-Phos 117 catalysis. The bicyclic acetals were delivered in good yields with high stereoselectivities (40-90%, up to > 20 : 1 dr, 85-99% ee).…”
Section: Enantioselective Annulation Reactions Of δ-Aryl (Alkyl) Alle...mentioning
confidence: 99%
“…For instance, the Wu group reported an Et 3 N-mediated bicyclization of triketone enones with malononitrile for the synthesis of fused furofuran compounds in 2013 (Scheme A). Recently, the Lu group developed a phosphine-catalyzed domino transformation of triketone enones with γ-substituted allenoates to form bicyclic furofurans in good yields with excellent enantioselectivities (Scheme B). Very recently, our group disclosed CPA-catalyzed regio-reversed domino processes of triketone enones with azlactones, giving a variety of bicyclic furofurans bearing vicinal quaternary carbons with good enantioselectivities (Scheme C).…”
Section: Introductionmentioning
confidence: 99%