104683-46-7Relevant academic research and scientific papers
Enantioselective anti- And syn-(borylmethyl)allylation of aldehydes via br?nsted acid catalysis
Liu, Jiaming,Chen, Ming
, p. 8967 - 8972 (2020)
The enantioselective anti- and syn-(borylmethyl)allylation of aldehydes via phosphoric acid catalysis is reported. Both (E)- and (Z)-γ-borylmethyl allylboronate reagents were prepared via the Cu-catalyzed highly stereoselective protoboration of 1,3-dienyl
Nickel-catalyzed borylative ring opening of vinyl epoxides and aziridines
Crotti, Stefano,Bertolini, Ferruccio,Macchia, Franco,Pineschi, Mauro
scheme or table, p. 3762 - 3765 (2011/03/19)
Image Presented A mild ring opening of vinyl epoxides and aziridines with B2Pin2 catalyzed by Ni(0)-Binap affords new functionalized allylic boron derivatives which undergo sequential transformations. The uncatalyzed allylation of al
Palladium-catalyzed carbonyl allylation by allylic alcohols with SnCl2
Takahara, Jun P.,Masuyama, Yoshiro,Kurusu, Yasuhiko
, p. 2577 - 2586 (2007/10/02)
Allylic alcohols can be applied to carbonyl allylation via the formation of π-allylpalladium complexes, using palladium as catalyst and SnCl2 as a reducing agent. This reaction has chemoselectivity: The reactivity order of allylating agents is allylic carbonate > allylic alcohol > allylic acetate, and that of carbonyl compounds is aldehyde > ketone. High regioselcction was observed in polar solvents such as DMF, DMI, and DMSO; carbonyl compounds apparently attacked the more substituted allylic position of π-allylpalladium complexes to afford only one regioisomer. Diastereocontrol in the carbonyl allylation of aromatic aldehydes by (E)-2-butenol was achieved by the choice of polar solvents; use of DMSO at 25 °C led to syn selection, while anti selection was found at -10 °C in THF. The addition of H2O in any solvent accelerated the carbonyl allylation and enhanced both regioselectivity and the diastereoselectivity. Anti selection in DMF, DMI, and THF-H2O can be explained by the chair form of the six-membered cyclic transition state, while syn selection in DMSO allows us to propose an acyclic antiperiplanar transition state. An NMR spectroscope investigation demonstrated that the actual allylating agent in dry medium was allyltrichlorotin: 1H, 13C, and 119Sn NMR spectra of the reaction of allyl alcohol with PdCl2(PhCN)2-SnCl2 in DMF-d7. corresponded to those of the reaction of allyl chloride with PdCl2(PhCN)2-SnCl2 in DMF-d7.
Palladium-catalyzed carbonyl allylation by 2-(hydroxymethyl)acrylate derivatives: Synthesis of α-methylene-γ-butyrolactones
Masuyama,Nimura,Kurusu
, p. 225 - 228 (2007/10/02)
Ethyl 2-(hydroxymethyl)acrylate derivatives serve as reagents for 2-ethoxycarnonylallylation of carbonyl compounds using PdCl2(PhCN)2-SnCl2 system to produce α-methylene-γ-butyrolactones diastereoselectively.
