Palladium-Catalyzed Asymmetric Benzylic Alkylation of Active Methylene Compounds with α-Naphthylbenzyl Carbonates and Pivalates

2016 ◽  
Vol 128 (24) ◽  
pp. 7087-7091 ◽  
Author(s):  
Sho Tabuchi ◽  
Koji Hirano ◽  
Masahiro Miura
Keyword(s):  
Active Methylene Compounds ◽  
Palladium Catalyzed ◽  
Active Methylene

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 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.

Triethylborane as an efficient promoter for palladium-catalyzed allylation of active methylene compounds with allyl alcohols

Tetrahedron ◽  
2003 ◽  
Vol 59 (39) ◽  
pp. 7767-7777 ◽  
Author(s):  
Masanari Kimura ◽  
Ryutaro Mukai ◽  
Naoko Tanigawa ◽  
Shuji Tanaka ◽  
Yoshinao Tamaru
Keyword(s):  
Active Methylene Compounds ◽  
Palladium Catalyzed ◽  
Allyl Alcohols ◽  
Active Methylene
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