scholarly journals Formal [3+2] Cycloaddition Reactions of Electron-Rich Aryl Epoxides with Alkenes under Lewis Acid Catalysis Affording Tetrasubstituted Tetrahydrofurans

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 692
Author(s):  
Víctor E. Macías-Villamizar ◽  
Luís Cuca-Suárez ◽  
Santiago Rodríguez ◽  
Florenci V. González
Keyword(s):  
Chemical Reaction ◽  
Lewis Acid ◽  
Acid Catalysis ◽  
Stereoselective Synthesis ◽  
Cycloaddition Reaction ◽  
Cycloaddition Reactions ◽  
Lewis Acid Catalysis

We report on the regio- and stereoselective synthesis of tetrahydrofurans by reaction between epoxides and alkenes in the presence of a Lewis acid. This is an unprecedented formal [3+2] cycloaddition reaction between an epoxide and an alkene. The chemical reaction represents a very concise synthesis of tetrahydrofurans from accessible starting compounds.

scholarly journals Stereoselective synthesis of bicyclo[3.n.1]alkenone frameworks by Lewis acid-catalysis

2017 ◽  
Vol 53 (82) ◽  
pp. 11353-11356 ◽  
Author(s):  
Stalin R. Pathipati ◽  
Lars Eriksson ◽  
Nicklas Selander
Keyword(s):  
Lewis Acid ◽  
Acid Catalysis ◽  
Stereoselective Synthesis ◽  
Lewis Acid Catalysis ◽  
Cyclic Ketones

An indium-catalysed α,α′-annulation of cyclic ketones and alkynyl enones, leading to bicyclo[3.n.1]alkenones, is presented.

Cycloaddition Reactions of the Methano[10]annulene Derivative 9,9-Dichloro-1,4-dihydro-4a,8a-methanonaphthalene

1991 ◽  
Vol 44 (4) ◽  
pp. 555 ◽  
Author(s):  
B Halton ◽  
SGG Russell
Keyword(s):  
Maleic Anhydride ◽  
Lewis Acid ◽  
Acid Catalysis ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
Lewis Acid Catalysis ◽  
Inverse Electron Demand ◽  
Hydrophilic Solvent ◽  
Electron Demand

9,9-Dichloro-1,4-dihydro-4a,8a-methanonaphthalene (4) adds the electron-deficient dienophiles 4-phenyl-1,2,4-triazoline-3,5-dione, maleic anhydride and dimethyl acetylenedicarboxylate to the α-face to give adducts (5)-(7) respectively; the addition of the alkyne requires Lewis acid catalysis. Inverse electron-demand addition of 3,6-diphenyl-1,2,4,5-tetrazine to the monoene component of (4) in hydrophilic solvent (ethane-1,2-diol) is thwarted; the CCl2 bridge is ejected and the 1,4-dihydronaphthalene formed is captured to give (ultimately) phthalazine (16). Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate adds to (4) to give the methanobenzophthalazine (17b).

Chiral Lewis Acid Catalysis in Nitrile Oxide Cycloadditions

2004 ◽  
Vol 126 (17) ◽  
pp. 5366-5367 ◽  
Author(s):  
Mukund P. Sibi ◽  
Kennosuke Itoh ◽  
Craig P. Jasperse
Keyword(s):  
Lewis Acid ◽  
Acid Catalysis ◽  
Nitrile Oxide ◽  
Lewis Acid Catalysis ◽  
Chiral Lewis Acid

Lewis Acid Catalysis with Cationic Dinuclear Gold(II,II) and Gold(III,III) Phosphorus Ylide Complexes

2016 ◽  
Vol 35 (17) ◽  
pp. 2830-2835 ◽  
Author(s):  
Benjamin R. Reiner ◽  
Mark W. Bezpalko ◽  
Bruce M. Foxman ◽  
Casey R. Wade
Keyword(s):  
Lewis Acid ◽  
Acid Catalysis ◽  
Lewis Acid Catalysis ◽  
Phosphorus Ylide ◽  
Ylide Complexes
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