2014
DOI: 10.1021/ol502365r
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Chiral Spirooxindole–Butenolide Synthesis through Asymmetric N-Heterocyclic Carbene-Catalyzed Formal (3 + 2) Annulation of 3-Bromoenals and Isatins

Abstract: By using an N-heterocyclic carbene catalyst bearing a hydroxyl moiety, the asymmetric formal (3 + 2) cyclization of aryl 3-bromoenals and isatins was achieved to produce a series of chiral spirooxindole-butenolides including an alkenyl-substituted compound, which underwent benzannulations with benzynes to form intriguing spirocyclic scaffolds.

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Cited by 67 publications
(15 citation statements)
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“…As a result, enormous efforts were devoted to building this scaffold,9 especially the chiral 3,3′‐spirocyclic oxindoles fused with a heterocycle structure. Several enantioselectively synthetic approaches such as 1,3‐dipolar cycloaddition11a,b or NHC‐catalyzed formal [3+2] annulation,10d,e,f have been designed to synthesize spiro oxa10 and spiro aza11 heterocycle oxindoles. However, only few asymmetric routes to synthesize the spiro tetrahydrothiophene oxindoles have been disclosed 12,13.…”
Section: Methodsmentioning
confidence: 99%
“…As a result, enormous efforts were devoted to building this scaffold,9 especially the chiral 3,3′‐spirocyclic oxindoles fused with a heterocycle structure. Several enantioselectively synthetic approaches such as 1,3‐dipolar cycloaddition11a,b or NHC‐catalyzed formal [3+2] annulation,10d,e,f have been designed to synthesize spiro oxa10 and spiro aza11 heterocycle oxindoles. However, only few asymmetric routes to synthesize the spiro tetrahydrothiophene oxindoles have been disclosed 12,13.…”
Section: Methodsmentioning
confidence: 99%
“…In 2014, Ma group illustrated an asymmetric formal [3+2] annulation of aryl 3-bromoenals 58 and isatins 10 to produce spirooxindole–butenolides 59 in excellent yield with high enantioselectivity through hydrogen-bonding activation-assisted chiral NHC catalysis ( Scheme 17 ). This reaction provides excellent yield (85–99%) and high enantioselectivity (93:7–96:4 er) [ 54 ].…”
Section: Nhc-catalyzed Synthesis Of Spiroheterocyclesmentioning
confidence: 99%
“…For the NHC‐catalyzed synthesis of 3‐spirooxindole lactones, restricted by the enals’ structure, most of the products are tricyclic 3‐spirooxindole lactones (Scheme 1, eq 1–2) [17] . Methods for the construction of the tetracyclic 3‐spirooxindole fused‐γ‐lactone derivatives are still limited, only a few reported examples include: i) benzannulation of 3‐styryl spirooxindole butenolides with benzynes [17g] ii) intramolecular annulation of specific benzoic acid derivative [18] . In 2018, Enders reported an asymmetric synthesis of tetracyclic spirooxindole‐ϵ‐lactones through NHC Catalysis of isatin‐derived enals and o ‐hydroxyphenylsubstituted p ‐quinone methides [19] .…”
Section: Introductionmentioning
confidence: 99%