1,3-Dipolar cycloaddition of α-alkoxycarbonylnitrones with vinyl ethers and allyl alcohols in the presence of Eu(fod)3: selective activation of (Z)-isomers of the nitrones

Tetrahedron ◽  
2006 ◽  
Vol 62 (52) ◽  
pp. 12227-12236 ◽  
Author(s):  
Osamu Tamura ◽  
Naka Mita ◽  
Yasuharu Imai ◽  
Takuya Nishimura ◽  
Tamiko Kiyotani ◽  
...  
Keyword(s):  
Dipolar Cycloaddition ◽  
Vinyl Ethers ◽  
Selective Activation ◽  
Allyl Alcohols

ChemInform Abstract: Chelation Controlled 1,3-Dipolar Cycloaddition of 5,6-Dihydro-5-phenyl-1,4-oxazin-2-one N-Oxide with Allyl Alcohols: A Short-Step Synthesis of Clavalanine Intermediate.

ChemInform ◽  
2010 ◽  
Vol 30 (20) ◽  
pp. no-no
Author(s):  
Osamu Tamura ◽  
Takahiro Kuroki ◽  
Yuta Sakai ◽  
Jun-ichi Takizawa ◽  
Jun Yoshino ◽  
...  
Keyword(s):  
Dipolar Cycloaddition ◽  
Allyl Alcohols

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

scholarly journals Palladium-catalyzed selective activation of allyl alcohols as allyl cations, allyl anions, and zwitterionic trimethylenemethanes

2008 ◽  
Vol 80 (5) ◽  
pp. 979-991 ◽  
Author(s):  
Yoshinao Tamaru ◽  
Masanari Kimura
Keyword(s):  
Catalytic System ◽  
Allylic Alcohols ◽  
Selective Activation ◽  
Active Methylene Compounds ◽  
Palladium Catalyzed ◽  
Synthetic Equivalent ◽  
Vinyl Epoxide ◽  
Allyl Alcohols ◽  
Allyl Anions ◽  
Active Methylene

Pd-Et3B catalytic system promotes the generation of allyl cations, allyl anions, and zwitterionic trimethylenemethane species from the corresponding allylic alcohols. Allyl cations react with a wide variety of nucleophiles, e.g., amines, active methylene compounds, 1,3,5-trihydroxybenzene, indoles, aldehydes (at the α-position). The reaction is extended to dehydrative Grob fragmentation of 1,3-diols. Allyl anions react with aldimines to give homoallyl amines. Zwitterionic trimethylenemethane, generated from 2-methylene-1,3-propanediol, reacts with aldehydes and aldimines to provide 3-methylenecyclopentanols and 3-methylenepyrrolidines, respectively. Vinyl epoxide can be utilized as a synthetic equivalent of 3-butenyl 2-anion-1-cation.

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