22056-09-3Relevant articles and documents
Enantioselective Lewis base catalyzed phosphonyldifluoromethylation of allylic fluorides using a: C -silyl latent pronucleophile
Zi, You,Lange, Markus,Vilotijevic, Ivan
supporting information, p. 5689 - 5692 (2020/06/19)
The first enantioselective phosphonyldifluoromethylation is enabled by the use of diethyl (difluoro(trimethylsilyl)-methyl)phosphonate reagent as a latent pronucleophile in the Lewis base catalyzed substitution of allylic fluorides. The reaction proceeds
Organocatalytic Allylic Amination of Morita-Baylis-Hillman Carbonates
Formánek, Bed?ich,?imek, Michal,Kamlar, Martin,Císa?ová, Ivana,Vesely, Jan
, p. 907 - 920 (2019/02/10)
An organocatalytic asymmetric allylic amination of Morita-Baylis-Hillman carbonates with aromatic amines in the presence of β-isocupreidine is described. Chiral allylic amines were obtained in almost quantitative yields (90-96%) with moderate enantioselectivity. Recrystallization afforded products in good yields (45-73%) and high optical purity (82-99% ee). This method provides a facile and efficient route to obtain optically active β-lactams, including the building block of the cholesterol-lowering drug Ezetimibe.
Enantioselective dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman carbonates
Yang, Xin-He,Li, Jian-Ping,Wang, Dong-Chao,Xie, Ming-Sheng,Qu, Gui-Rong,Guo, Hai-Ming
supporting information, p. 9144 - 9147 (2019/08/07)
The phosphine-catalyzed asymmetric dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman (MBH) carbonates or allenoate was developed. The reaction with MBH carbonates resulted in a series of cyclopentabenzofurans containing three contiguous stereocenters with good to high yields, diastereoselectivities and enantioselectivities. The use of allenoate also gave the target product with moderate enantioselectivity.
Decarboxylative Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbamates
Do?ekal, Vojtěch,?imek, Michal,Dra?ínsky, Martin,Vesely, Jan
supporting information, p. 13441 - 13445 (2018/09/21)
The present study reports the organocatalytic enantioselective allylic amination of Morita–Baylis–Hillman carbamates efficiently catalyzed by a chiral amine in the presence of a Br?nsted acid. Chiral allylic amines were produced in high yields (up to 98 %) and enantioselectivities (up to 97 % ee). This method provides an efficient and easily performed route to prepare α-methylene-β-lactams, and other optically active β-lactams, such as the cholesterol-lowering drug Ezetimibe.
Star-like polyionic heterogeneous nanocatalyst as a highly active catalyst for promotion of Baylis-Hillman reaction in [bmim]Cl
Valizadeh, Hassan,Shomali, Ashkan,Noorshargh, Saeideh
, p. 2169 - 2177 (2015/10/19)
The use of star-like polyionic Lewis base heterogeneous nanocatalyst for the Baylis-Hillman reaction of benzyl- and methylacrylates with aryl aldehydes has been investigated. The corresponding Baylis-Hillman adducts are obtained in good to high yields in
Ferrocenylphosphines as new catalysts for Baylis-Hillman reactions
Pereira, Susana Isabel,Adrio, Javier,Silva, Artur M. S.,Carretero, Juan Carlos
, p. 10175 - 10177 (2007/10/03)
Readily available ferrocenyldialkylphosphines are effective air-stable catalysts for Baylis-Hillman reaction between aldehydes and acrylates, affording the corresponding adducts in high yields and short reaction times. A set of readily accessible planar c
A remarkable rate acceleration of the Baylis-Hillman reaction
Lee,Yang,Chen
, p. 1612 - 1613 (2007/10/03)
Treatment of α-naphthyl acrylate with both aliphatic and aromatic aldehydes in the presence of DABCO (30 mol%) afforded the desired (α-methylene-β-hydroxy)esters with reasonable chemical yields (51-88%) within 20 min.
The 'Baylis - Hillman reaction' mechanism and applications revisited
Fort, Yves,Berthe, Marie Christine,Caubere, Paul
, p. 6371 - 6384 (2007/10/02)
It is shown that reaction of aryl, benzyl, alkyl and functionalised alkyl acrylic esters with benzaldehyde, in the presence of 1,4-diazabicyclo[2.2.2] octane, strongly depends upon the electronic and steric effects of the ester part. This influence is also observed in condensation of furfuraldehyde. Moreover, for the first time, it is shown that the overall condensation is equilibrated.
