Lewis acid mediated Michael addition of non-aromatic multiple C C bonds to α,β-unsaturated dicarbonyl compounds

Denisov, Dmitry A.; Новиков, Роман А.; Tomilov, Yury V.

doi:10.1016/j.tetlet.2021.153272

Cited by 6 publications

(4 citation statements)

References 28 publications

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“…Metal halide promoted intra‐ and intermolecular reactions of alkyne with highly electrophilic olefins such as ene‐diesters and ene‐triesters are synthetically useful generating carbo‐ and heterocycles [22] . In general, these reactions require stoichiometric amount of metal halides (MX n : M=Fe, Zn, Ga; X=Cl, Br, I) and are largely developed due to pioneering work of Snider [23] and Yamazaki [24] .…”

Section: Introductionmentioning

confidence: 99%

“…Metal halide promoted intra-and intermolecular reactions of alkyne with highly electrophilic olefins such as ene-diesters and ene-triesters are synthetically useful generating carbo-and heterocycles. [22] In general, these reactions require stoichiometric amount of metal halides (MX n : M=Fe, Zn, Ga; X=Cl, Br, I) and are largely developed due to pioneering work of Snider [23] and Yamazaki. [24] Recently, Novikov, Tomilov and co-workers demonstrated a new concept of utilizing dialkyl β-arylidenemalonates as 1,2-zwitterionic synthons in the presence of stoichiometric amount of gallium halides for various useful synthetic transformations including the synthesis of indenes and lactones.…”

Section: Introductionmentioning

confidence: 99%

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Catalytic Cycloisomerization of Enyne Diesters Derived from Biaryls and Related Substrates

et al. 2023

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Enyne diesters derived from biaryls and related substrates undergo intramolecular [2 + 2]cycloaddition and concomitant cyclo-reversion when treated with 10 mol% In(OTf) 3 in 1,2-dichloroethane. This enyne metathesis type cycloisomerization reaction enables the synthesis of phenanthrene, benzophenanthrene, benzotetraphene and other polycyclic (hetero)aromatic compounds bearing a synthetically useful diethyl β-(hetero)arylidene malonate moiety in a step-and atom-economic manner. In(OTf) 3 -catalyzed two independent intramolecular cycloisomerization on substrates 5 a and 5 b provides direct access to benzotetraphenes 6 a and 6 b containing bis(diethyl β-phenylmethylene malonate) moiety. Tetrasubstituted vinylidene malonate 4 a, substiututed by two different aromatic groups, is stereoselectively converted into Eand Z-isomer of triaryl group containing all carbon tetrasubstituted olefins (8 a, 8 a' and 8 b) via Pd-catalyzed stereoselective decarboxylative arylation reaction.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Catalytic Cycloisomerization of Enyne Diesters Derived from Biaryls and Related Substrates

et al. 2023

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“…Transition metal halides promoted enyne diester cyclization is an important method for annulation providing access to carbo-and heterocycles. [1][2][3][4][5][6] The requisites of this type of cyclization are an electrophilic alkene (such as diethyl 2-arylidene malonate) bearing coordination site for metal halides and an alkyne which acts as the nucleophile. While the analogous ene-ene cyclization [7][8][9][10][11][12][13][14][15][16] is facile, enyne cyclization is less facile due to low nucleophilicity of alkyne and thus often requires highly electrophilic olefin containing three electron-withdrawing groups.…”

Section: Introductionmentioning

confidence: 99%

“…Transition metal halides promoted enyne diester cyclization is an important method for annulation providing access to carbo‐ and heterocycles [1–6] . The requisites of this type of cyclization are an electrophilic alkene (such as diethyl 2‐arylidene malonate) bearing coordination site for metal halides and an alkyne which acts as the nucleophile.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Cycloisomerization of Enyne Diesters Derived From 2‐Propargyloxyarylaldehydes

2022

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A catalytic cycloisomerization of enyne diesters derived from 2-propargyloxyarylaldehydes is described. The cycloisomerization, catalyzed by 10 mol% In(OTf) 3 , provides access to 2H-chromenes bearing diethyl 2-(hetero)arylidene malonates at 3-position. This enyne metathesis-type reaction is also useful for the synthesis of thia-, aza-and quinoline analogs of the 3-substituted 2H-chromenes. DDQ mediated oxidative CÀ N bond formation and further synthetic manipulation enables the conversion of 3-substituted 2H-chromene into chromene-fused molecular scaffold. Pd(0)-catalyzed intramolecular Heck reaction on suitably substituted 2H-chromene provides indene-based molecular scaffold.

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Ring‐Opening Cyclization of Spirocyclopropanes with Stabilized Phosphorus Ylides: Access to Indane and Azulene Skeletons

et al. 2023

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In this study, regio‐ and diastereoselective ring‐opening cyclization of spirocyclopropanes with phosphorus ylides stabilized by electron‐withdrawing groups were developed. The reaction of various cyclohexane‐1,3‐dione‐2‐spirocyclopropanes with phosphorus ylides bearing alkoxycarbonyl groups proceeded smoothly without any additives to provide the corresponding 6,7‐dihydroindan‐4‐ones in 32–87% yields. Cycloheptane‐1,3‐dione‐2‐spirocyclopropanes were also used in this reaction, producing the corresponding products 1,2,3,6,7,8‐hexahydroazulen‐4‐ones in 52–67% yields. The resulting [5.6]‐ and [5.7]‐fused carbocyclic products were readily converted into highly substituted indanes and azulenes, respectively, by oxidation.

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Lewis acid mediated Michael addition of non-aromatic multiple C C bonds to α,β-unsaturated dicarbonyl compounds

Cited by 6 publications

References 28 publications

Catalytic Cycloisomerization of Enyne Diesters Derived from Biaryls and Related Substrates

Catalytic Cycloisomerization of Enyne Diesters Derived from Biaryls and Related Substrates

Catalytic Cycloisomerization of Enyne Diesters Derived From 2‐Propargyloxyarylaldehydes

Ring‐Opening Cyclization of Spirocyclopropanes with Stabilized Phosphorus Ylides: Access to Indane and Azulene Skeletons

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