Activation of Allyl Alcohols as Allyl Cations, Allyl Anions, and Amphiphilic Allylic Species by Palladium

ChemInform ◽  
2005 ◽  
Vol 36 (40) ◽  
Author(s):  
Yoshinao Tamaru
Keyword(s):  
Allyl Alcohols ◽  
Allyl Anions

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.

ChemInform Abstract: COHALOGENATION OF OLEFINS: APPLICATION TO THE SYNTHESIS OF ALLYL ALCOHOLS

1984 ◽  
Vol 15 (21) ◽  
Author(s):  
J. RODRIGUEZ ◽  
J.-P. DULCERE ◽  
M. BERTRAND
Keyword(s):  
Allyl Alcohols

ChemInform Abstract: Fast and Highly Regioselective Allylation of Indole and Pyrrole Compounds by Allyl Alcohols Using Ru-Sulfonate Catalysts.

ChemInform ◽  
2009 ◽  
Vol 40 (2) ◽  
Author(s):  
Alexey B. Zaitsev ◽  
Stefan Gruber ◽  
Pascal A. Pluess ◽  
Paul S. Pregosin ◽  
Luis F. Veiros ◽  
...  
Keyword(s):  
Allyl Alcohols

A versatile route to silylsubstituted ketones by rhodium catalyzed isomerization of silylated allyl alcohols

1984 ◽  
Vol 25 (7) ◽  
pp. 769-770 ◽  
Author(s):  
Susumu Sato ◽  
Hisashi Okada ◽  
Isamu Matsuda ◽  
Yusuke Izumi
Keyword(s):  
Allyl Alcohols
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