On the solvent‐ and temperature‐driven stereoselectivity of the Diels–Alder cycloaddition reactions of furan with maleic anhydride and maleimide

2020 ◽  
Author(s):  
Veejendra K. Yadav ◽  
Dasari L.V.K. Prasad ◽  
Arpita Yadav ◽  
Kedar Yadav
Keyword(s):  
Maleic Anhydride ◽  
Diels Alder ◽  
Cycloaddition Reactions

Synthesis of functionalized hexahydro-, octahydro-, and decahydro-1H-phenalenes via Diels–Alder reactions of 1-methylene-4a-methoxycarbonyl-1,2,3,4,4a,5,6,7-octahydronaphthalene and related dienes

1993 ◽  
Vol 71 (9) ◽  
pp. 1463-1483 ◽  
Author(s):  
Edward Piers ◽  
Richard W. Friesen ◽  
Paul Kao ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Maleic Anhydride ◽  
Transition State ◽  
Methyl Acrylate ◽  
Diels Alder ◽  
Cycloaddition Reactions ◽  
Methoxycarbonyl Group ◽  
The Face ◽  
Group Reaction ◽  
Bicyclic Dienes

The results of a study of Diels–Alder reactions of the bicyclic dienes 6–8 with a variety of dienophiles are reported. Although 6 and 7 undergo cycloaddition reactions smoothly and efficiently, thermal Diels–Alder reactions of 8 are generally sluggish or, under the conditions investigated, do not proceed at all. Additions of tetracyanoethylene (TCNE) to 6–8 are highly face-selective, with preferential attack of the dienophile on the side of the dienes opposite to the angular methoxycarbonyl group. Reaction of 7 with maleic anhydride (MAN) is completely face-selective and proceeds preferentially via an endo transition state. Diels–Alder reactions of 6 and 7 with methyl acrylate (MAC) and nitroethylene (NE) are entirely regioselective, but the face-selectivities, which vary from ~2:1 to ~3:1, are rather low. The use of this chemistry as a method for the synthesis of functionalized, stereochemically defined, perhydro-1H-phenalenes is demonstrated.

E,E- and E,Z-α-phenyl-α′-acetoxyorthoquinodimethane: steric and electronic control of cycloaddition reactions

1986 ◽  
Vol 64 (4) ◽  
pp. 793-798 ◽  
Author(s):  
James L. Charlton ◽  
Mian M. Alauddin ◽  
Glenn H. Penner
Keyword(s):  
Maleic Anhydride ◽  
Electronic Properties ◽  
Dimethyl Fumarate ◽  
Diels Alder ◽  
Addition Reactions ◽  
Cycloaddition Reactions ◽  
Electronic Control ◽  
Dimethyl Maleate ◽  
Cis And Trans ◽  
Abinitio Calculations

E,E- and E,Z-α-phenyl-α′-acetoxyorthoquinodimethanes have been prepared from the corresponding cis- and trans-1-acetoxy-3-phenyl-1,3-dihydrobenzo[c]thiophene-2,2-dioxides. The regio- and diastereoselectivity of the addition reactions with dimethyl fumarate, dimethyl maleate, maleic anhydride, and methyl crotonate have been determined. Abinitio calculations have been carried out on orthoquinodimethane and its α-phenyl and α-oxy derivatives. A correlation has been made between the steric and electronic properties of the orthoquinodimethanes and the regio- and diastereoselectivity of their Diels–Alder reactions.

Asymmetric Diels-Alder reactions with a chiral maleic anhydride analog, 5-(1-menthyloxy)-2(5H)-furanone

1988 ◽  
Vol 53 (5) ◽  
pp. 1125-1127 ◽  
Author(s):  
Ben L. Feringa ◽  
Johannes C. De Jong
Keyword(s):  
Maleic Anhydride ◽  
Diels Alder

scholarly journals Kinetic Analysis of the High-pressure Diels-Alder Reactions of Tropone with Maleic Anhydride and Norbornene

1985 ◽  
Vol 58 (9) ◽  
pp. 2490-2493 ◽  
Author(s):  
Hitoshi Takeshita ◽  
Shigeru Sugiyama ◽  
Toshihide Hatsui
Keyword(s):  
High Pressure ◽  
Maleic Anhydride ◽  
Kinetic Analysis ◽  
Diels Alder

Hetero-Diels-Alder Reactions of Enaminothione with Electrophilic Olefins. Synthesis of 2-Furyl Substituted 2H-Thiopyrans

2002 ◽  
Vol 57 (6) ◽  
pp. 637-644 ◽  
Author(s):  
Krystyna Bogdanowicz-Szwed ◽  
Artur Budzowski
Keyword(s):  
Acetic Acid ◽  
Maleic Anhydride ◽  
Acetic Anhydride ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diethyl Maleate ◽  
Diels Alder Reaction

AbstractThe hetero-Diels-Alder reaction of 1-(2-furyl)-3-(dimethylamino)-2-propene-1-thione (diene) with maleic and fumaric acids, and β-nitrostyrenes yielded 3,4-dihydro-2H-thiopyran derivatives. Treatment of some of those cycloadducts with acetic acid caused elimination of dimethylamine yielding stable 2H-thiopyrans. Reaction of the diene with maleic anhydride furnished a cycloadduct which underwent spontaneous rearrangement to form an N,N-dimethylamide derivative. Cycloadditions of the diene to maleimide, N-phenylmaleimide, diethyl maleate, fumarate and butenolide, carried out in the presence of acetic anhydride,were followed by elimination of dimethylamine, afforded stable 2H-thiopyran derivatives.

A New Series of Organocatalysts for Diels-Alder Cycloaddition Reactions and Theoretical Analysis

2011 ◽  
Vol 15 (19) ◽  
pp. 3514-3522 ◽  
Author(s):  
Alessandro Casoni ◽  
Elena Borsini ◽  
Alessandro Contini ◽  
Alessandro Ruffoni ◽  
Sara Pellegrino ◽  
...  
Keyword(s):  
Theoretical Analysis ◽  
Diels Alder ◽  
Cycloaddition Reactions
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