ChemInform Abstract: Palladium-Catalyzed Selective Activation of Allyl Alcohols as Allyl Cations, Allyl Anions, and Zwitterionic Trimethylenemethanes

ChemInform ◽  
2008 ◽  
Vol 39 (43) ◽  
Author(s):  
Yoshinao Tamaru ◽  
Masanari Kimura
Keyword(s):  
Selective Activation ◽  
Palladium Catalyzed ◽  
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.

Palladium-Catalyzed Amination of Allyl Alcohols

2011 ◽  
Vol 76 (20) ◽  
pp. 8508-8512 ◽  
Author(s):  
Raju Ghosh ◽  
Amitabha Sarkar
Keyword(s):  
Palladium Catalyzed ◽  
Allyl Alcohols

Triethylborane as an Efficient Promoter for Palladium-Catalyzed Allylation of Active Methylene Compounds with Allyl Alcohols.

ChemInform ◽  
2004 ◽  
Vol 35 (3) ◽  
Author(s):  
Masanari Kimura ◽  
Ryutaro Mukai ◽  
Naoko Tanigawa ◽  
Shuji Tanaka ◽  
Yoshinao Tamaru
Keyword(s):  
Active Methylene Compounds ◽  
Palladium Catalyzed ◽  
Allyl Alcohols ◽  
Active Methylene

scholarly journals Palladium-Catalyzed Allylation of Imines with Allyl Alcohols.

ChemInform ◽  
2005 ◽  
Vol 36 (27) ◽  
Author(s):  
Masamichi Shimizu ◽  
Masanari Kimura ◽  
Toshiya Watanabe ◽  
Yoshinao Tamaru
Keyword(s):  
Palladium Catalyzed ◽  
Allyl Alcohols
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