A simple and efficient FeCl3-catalyzed direct alkylation of active methylene compounds with benzylic and allylic alcohols under mild conditions

2007 ◽  
Vol 48 (23) ◽  
pp. 4065-4069 ◽  
Author(s):  
Umasish Jana ◽  
Srijit Biswas ◽  
Sukhendu Maiti
Keyword(s):  
Allylic Alcohols ◽  
Mild Conditions ◽  
Active Methylene Compounds ◽  
Active Methylene

Et3B-promoted, Pd(0)-catalyzed allylation of active methylene compounds with allylic alcohols

2000 ◽  
Vol 41 (30) ◽  
pp. 5705-5709 ◽  
Author(s):  
Yoshinao Tamaru ◽  
Yoshikazu Horino ◽  
Misato Araki ◽  
Shuji Tanaka ◽  
Masanari Kimura
Keyword(s):  
Allylic Alcohols ◽  
Active Methylene Compounds ◽  
Active Methylene

ChemInform Abstract: Et3B-Promoted, Pd(0)-Catalyzed Allylation of Active Methylene Compounds with Allylic Alcohols.

ChemInform ◽  
2000 ◽  
Vol 31 (44) ◽  
pp. no-no
Author(s):  
Yoshinao Tamaru ◽  
Yoshikazu Horino ◽  
Misato Araki ◽  
Shuji Tanaka ◽  
Masanari Kimura
Keyword(s):  
Allylic Alcohols ◽  
Active Methylene Compounds ◽  
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.

Et3N-Promoted Tandem Cyclization of Bromomaleimides with Active Methylene Compounds: An Efficient Synthesis of cis-3,4-Dihydropyrrolidine-2,5-diones

Synlett ◽  
2019 ◽  
Vol 30 (13) ◽  
pp. 1565-1572
Author(s):  
Mengyao Li ◽  
Yinghong Zhu ◽  
Haibin Wang ◽  
Wanli Chen
Keyword(s):  
Efficient Method ◽  
Efficient Synthesis ◽  
Mild Conditions ◽  
Active Methylene Compounds ◽  
Tandem Cyclization ◽  
Active Methylene

The Et3N-promoted tandem cyclization of bromomaleimides with active methylene compounds is presented, providing an efficient method for the synthesis of cis-3,4-dihydropyrrolidine-2,5-diones in moderate to good yields under mild conditions.

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