784144-71-4Relevant academic research and scientific papers
Phosphine-Catalyzed [3 + 2] Annulation of Morita-Baylis-Hillman Carbonates with Isoxazole-Based Alkenes
Liao, Jianning,Dong, Jipan,Xu, Jiaqing,Wang, Wei,Wu, Yongjun,Hou, Yuxia,Guo, Hongchao
supporting information, p. 2090 - 2099 (2021/02/05)
A phosphine-catalyzed [3 + 2] annulation of Morita-Baylis-Hillman (MBH) carbonates with 3-methyl-4-nitro-5-styrylisoxazoles has been developed to afford various multifunctional isoxazoles in moderate to good yields with moderate to excellent diastereoselectivities. With a spirocyclic chiral phosphine as the catalyst, up to 89% ee was obtained.
Ir-Catalyzed Asymmetric Hydrogenation of α-Alkylidene β-Lactams and Cyclobutanones
Xia, Jingzhao,Nie, Yu,Yang, Guoqiang,Liu, Yangang,Gridnev, Ilya D.,Zhang, Wanbin
supporting information, p. 612 - 618 (2018/06/22)
Chiral β-lactams and cyclobutanones are present in numerous natural and pharmaceutical products. The stereoselective construction of chiral four-membered cyclic compounds is an ongoing challenge for the chemical community. Herein, we report a highly stere
Factors influencing the cytotoxicity of α-methylene-γ-hydroxy esters against pancreatic cancer
Ramachandran, P. Veeraraghavan,Helppi, Matthew A.,Lehmkuhler, Arlie L.,Marchi, Jennifer M.,Schmidt, C. Max,Yip-Schneider, Michele T.
supporting information, p. 4270 - 4273 (2015/11/03)
A systematic study to identify the factors influencing the cytotoxicity of α-methylene-γ-hydroxy esters against three pancreatic cancer cell lines (Panc-1, MIA-PaCa-2, and BxPC-3) has established that, in addition to Michael acceptor abilities, the possibility to lactonize to α-methylene-γ-butyrolactones is as important. The substitution pattern and the number of carbons between the hydroxy and ester moieties also influence the bio-activity.
Synthesis, characterization and antimicrobial activity of some new Baylis-Hillman derived benzothiazolo pyrimidinone derivatives
Gampa, Raghavachary,Chebrolu, Lavanya Devi,Jarapula, Ravi,Vaidya, Jayathirtha Rao,Ghanakota, Venkateshwar Rao,Manda, Sarangapani
, p. 217 - 227 (2015/03/04)
A series of Baylis-Hillman derived 22 new benzothiazolo pyrimidinone derivatives have been synthesized from Baylis-Hillman acetates and 2-amino benzothiazole under neat conditions with high yields. All the newly synthesized compounds have been characteriz
Syntheses of β- And γ-fluorophenyl cis- and trans-α-methylene-γ-butyrolactones
Ramachandran, P. Veeraraghavan,Nair, Hari Narayanan G.,Gagare, Pravin
supporting information, p. 5722 - 5726 (2015/02/05)
Preparation of a series of cis-γ-fluorophenyl-β-phenyl-α-methylene-γ-butyrolactones is reported via 'allylboration' of fluorobenzaldehydes with (E)-methyl 3-phenyl-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)acrylate. The corresponding trans-γ-
A general approach to the synthesis of β2-amino acid derivatives via highly efficient catalytic asymmetric hydrogenation of α-aminomethylacrylates
Guo, Yujuan,Shao, Guang,Li, Lanning,Wu, Wenhao,Li, Ruihong,Li, Jingjing,Song, Jian,Qiu, Liqin,Prashad, Mahavir,Kwong, Fuk Yee
experimental part, p. 1539 - 1553 (2010/08/22)
A new strategy was developed for the synthesis of a valuable class of α-aminomethylacrylates via the Baylis-Hillman reaction of different aldehydes with methyl acrylate followed by acetylation of the resulting allylic alcohols and SN2′-type amination of the allylic acetates. Asymmetric hydrogenation of these diverse olefinic precursors using rhodium(Et-Duphos) catalysts provided the corresponding β2-amino acid derivatives with excellent enantioselectivities and exceedingly high reactivities (up to >99.5% ee and S/C=10,000). The first hydrogenation of (Z)-configurated substrates was studied for the synthesis of β2-amino acid derivatives. The high influence of the substrate geometry and steric hindrance on the reactivity and enantioselectivity was also disclosed for this reaction. This protocol provides a highly practical, facile and scalable method for the preparation of optically pure β2- amino acids and their derivatives under mild reaction conditions.
Synthesis of fluorinated glutamic acid derivatives via vinylalumination
Ramachandran, P. Veeraraghavan,Madhi, Sateesh,O'Donnell, Martin J.
, p. 78 - 83 (2008/03/13)
A variety of structural types of fluorinated allylic acetates, prepared by vinylalumination of fluorinated aldehydes, were reacted with the benzophenone imine of glycine tert-butyl ester to provide 4-(fluorobenzylidenyl)- and 4-(fluoroalkylidenyl) glutami
Novel application of phosphonium salts as co-catalysts for the Baylis-Hillman reaction
Johnson, Claire L.,Donkor, Rachel E.,Nawaz, Wafaa,Karodia, Nazira
, p. 7359 - 7361 (2007/10/03)
Excellent yields have been obtained when the Baylis-Hillman reaction is conducted in the presence of phosphonium salts.
