ChemInform Abstract: O-QUINONE METHIDES. 2. STEREOSELECTIVITY IN CYCLOADDITION REACTIONS OF O-QUINONE METHIDES WITH VINYL ETHERS

1985 ◽  
Vol 16 (47) ◽  
Author(s):  
A. ARDUINI ◽  
A. BOSI ◽  
A. POCHINI ◽  
R. UNGARO
Keyword(s):  
Cycloaddition Reactions ◽  
Vinyl Ethers ◽  
Quinone Methides

-quinone methides 2. Stereoselectivity in cycloaddition reactions of -quinone methides with vinyl ethers

Tetrahedron ◽  
1985 ◽  
Vol 41 (15) ◽  
pp. 3095-3103 ◽  
Author(s):  
Arturo Arduini ◽  
Anna Bosi ◽  
Andrea Pochini ◽  
Rocco Ungaro
Keyword(s):  
Cycloaddition Reactions ◽  
Vinyl Ethers ◽  
Quinone Methides

A New Cycloaddition Profile for ortho-Quinone Methides: Photoredox-Catalyzed [6+4] Cycloadditions for Synthesis of Benzo[b]cyclopenta[e]oxepines

2022 ◽  
Author(s):  
Kenta Tanaka ◽  
Yosuke Asada ◽  
Yujiro Hoshino
Keyword(s):  
Visible Light ◽  
Cycloaddition Reactions ◽  
Quinone Methides

Visible-light-induced [6+4] cycloaddition reactions of ortho-quinone methides have been developed. The reaction of ortho-quinone methides with pentafulvenes in the presence of a thioxanthylium photoredox catalyst afforded benzo[b]cyclopenta[e]oxepines. The present reaction...

Chemoselective acid-catalyzed [4 + 2]-cycloaddition reactions of ortho-quinone methides and styrenes/stilbenes/cinnamates

2020 ◽  
Vol 18 (43) ◽  
pp. 8854-8866
Author(s):  
Kornkamon Akkarasereenon ◽  
Kassrin Tangdenpaisal ◽  
Somsak Ruchirawat ◽  
Poonsakdi Ploypradith
Keyword(s):  
Cycloaddition Reactions ◽  
Quinone Methides ◽  
Acid Catalyzed

Chemoselective [4 + 2]-cycloaddition reactions between o-QMs and different olefins—styrenes, stilbenes, and cinnamates—yielded distinct cycloadducts in moderate to good yields.

1,2,4-Oxadiazole 4-Oxides as Nitrones in 1,3-Dipolar Cycloaddition Reactions to Vinyl Ethers

2012 ◽  
Vol 2012 (7) ◽  
pp. 1418-1425 ◽  
Author(s):  
Paolo Quadrelli ◽  
Fabio Lunghi ◽  
Bruna Bovio ◽  
William Gautschi ◽  
Pierluigi Caramella
Keyword(s):  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Vinyl Ethers

1,3-Dipolar cycloaddition reactions of nitrones with alkyl vinyl ethers catalyzed by chiral oxazaborolidines

Tetrahedron ◽  
1997 ◽  
Vol 53 (34) ◽  
pp. 11843-11852 ◽  
Author(s):  
Jean-Paul G. Seerden ◽  
Mike M.M. Boeren ◽  
Hans W. Scheeren
Keyword(s):  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Vinyl Ethers

[2 + 2] Cycloaddition Reactions of 1-Trifluoroacetyl-2-chloroacetylene with Vinyl Ethers

2005 ◽  
Vol 404 (4-6) ◽  
pp. 210-211 ◽  
Author(s):  
N. P. Tsvetkov ◽  
A. B. Koldobskii ◽  
I. A. Godovikov ◽  
V. N. Kalinin
Keyword(s):  
Cycloaddition Reactions ◽  
Vinyl Ethers

Furfuryl vinyl ethers in [4+2]-cycloaddition reactions

2017 ◽  
Vol 53 (2) ◽  
pp. 203-209 ◽  
Author(s):  
L. A. Oparina ◽  
O. V. Vysotskaya ◽  
A. V. Stepanov ◽  
I. A. Ushakov ◽  
K. A. Apartsin ◽  
...  
Keyword(s):  
Cycloaddition Reactions ◽  
Vinyl Ethers

Asymmetric induction in Diels–Alder reactions of α-alkoxyorthoquinodimethanes

1989 ◽  
Vol 67 (6) ◽  
pp. 1010-1014 ◽  
Author(s):  
James L. Charlton ◽  
Guy L. Plourde ◽  
Glenn H. Penner
Keyword(s):  
Molecular Orbital ◽  
Geometry Optimization ◽  
Diels Alder ◽  
Asymmetric Induction ◽  
Molecular Orbital Calculations ◽  
Cycloaddition Reactions ◽  
Vinyl Ethers ◽  
The Face ◽  
Face Selectivity ◽  
Alkoxy Groups

It has been shown that dienophiles cycloadd selectively to one face of o-quinodimethanes (o-QDMs) bearing chiral α-alkoxy groups. The face selectivity (diastereoselectivity) increases for the series of chiral groups -OCH(Ph)CH3, -OCH(Ph)CH(CH3)2, and -OCH(Ph)C(CH3)3. A similar effect on the face selectivity of the Diels–Alder reactions of chiral alkoxy vinyl ethers for the same series of chiral groups has been noted previously by others. A mechanism has been proposed to explain the face selectivity in the cycloaddition reactions of the alkoxy o-QDMs. Abinitio molecular orbital calculations with geometry optimization on vinyl 1-phenylethyl ether to determine its lowest energy conformations support the proposed mechanism. The absolute stereochemistries of the o-QDM cycloadducts have been determined to verify the predictions of the model. Keywords: o-quinodimethanes, asymmetric, Diels–Alder, cycloaddition.

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