87938-77-0Relevant articles and documents
Synthesis of Phostones via the Palladium-Catalyzed Ring Opening of Epoxy Vinyl Phosphonates
Gnawali, Giri Raj,Rath, Nigam P.,Spilling, Christopher D.
, p. 8724 - 8730 (2019/07/03)
The reaction of epoxy aldehydes with tetraethyl methylenediphosphonate gave γ,δ-epoxy vinyl phosphonates. The palladium-catalyzed addition of primary alcohols gave the monoprotected diols as single diastereoisomers. The trans- and cis-epoxides lead to opp
Organocatalytic asymmetric epoxidation and tandem epoxidation/Passerini reaction under eco-friendly reaction conditions
Deobald, Anna Maria,Corrêa, Arlene G.,Rivera, Daniel G.,Paix?o, Márcio Weber
supporting information, p. 7681 - 7684 (2013/04/24)
An eco-friendly synthesis of highly functionalized epoxides and their incorporation into an organocatalytic multicomponent approach are reported. For this, a modified class of diarylprolinol silyl ethers was designed to enable high catalytic activity in an environmentally benign solvent system. The one-pot procedure showed great efficiency in promoting stereoselective multicomponent transformations in a tandem, 'green' fashion. Because of its non-residual, efficient and selective character, this synthetic design shows promise for large-scale applications in both diversity and target-oriented syntheses. The Royal Society of Chemistry 2012.
Organocatalytic preparation of simple β-hydroxy and β-amino esters: Low catalyst loadings and gram-scale synthesis
Jiang, Hao,Gschwend, Bjoern,Albrecht, Lukasz,Anker Jorgensen, Karl
supporting information; experimental part, p. 5052 - 5055 (2010/12/25)
A combined amino- and N-heterocyclic carbene (NHC)-catalyzed one-pot reaction sequence for the synthesis of simple enantioenriched β-hydroxy and β-amino esters using commercially available catalysts at low catalyst loadings has been developed. The desired
Amine-catalyzed asymmetric epoxidation of α,β-unsaturated aldehydes
Zhao, Gui-Ling,Ibrahem, Ismail,Sunden, Henrik,Cordova, Armando
, p. 1210 - 1224 (2008/09/17)
The direct organocatalytic enantioselective epoxidation of α,β-unsaturated aldehydes with different peroxides is presented. Proline, chiral pyrrolidine derivatives, and amino acid-derived imidazolidinones catalyze the asymmetric epoxidation of α,β-unsatur
Organocatalytic asymmetric epoxidation reactions in water-alcohol solutions
Zhuang, Wei,Marigo, Mauro,Jorgensen, Karl Anker
, p. 3883 - 3885 (2007/10/03)
The diastereo- and enantioselective organocatalytic epoxidation of α,β-unsaturated aldehydes in aqueous solutions is presented. By the screening of the reaction conditions for the epoxidation of cinnamic aldehyde applying hydrogen peroxide as the oxidant and 2-[bis-(3,5-bis-trifluoromethyl- phenyl)-trimethylsilanyloxy-methyl]-pyrrolidine as the catalyst, a highly stereoselective reaction has been developed. The scope of the diastereo- and enantioselective organocatalytic epoxidation in aqueous solutions is documented by the asymmetric epoxidation of α,β-unsaturated aldehydes with enantioselectivities up to 96% ee. The Royal Society of Chemistry 2005.
Mukaiyama aldolisation reactions of α,β-epoxyaldehydes in aqueous media
Ruland, Yvan,Noereuil, Pierre,Baltas, Michel
, p. 8895 - 8903 (2007/10/03)
The Mukaiyama aldolisation reaction in aqueous media of cis and trans α,β-epoxyaldehydes with tert-butyldimethylsilyl ketene acetal in the presence of Lewis's acids was studied. Sc(OTf)3 gave the best results in terms of selectivity. The same r
Palladium-catalyzed stereospecific epoxide-opening reaction of γ,δ-epoxy-α,β-unsaturated esters with boric acid leading to γ,δ-diol derivatives with double inversion of configuration
Yu, Xiao-Qiang,Hirai, Atsushi,Miyashita, Masaaki
, p. 764 - 765 (2007/10/03)
A new palladium-catalyzed epoxide-opening reaction of γ,δ- epoxy-α,β-unsaturated esters with boric acid has been developed, which proceeds stereospecifically giving rise to the corresponding γ,β-diol derivatives with double inversion of the configuration, i.e., with retention of configuration, in excellent yields. The new method provides a useful tool in organic synthesis including natural product synthesis. (Graph Presented).
Palladium-catalyzed stereospecific epoxide-opening reaction of γ,δ-epoxy-α,β-unsaturated esters with an alkylboronic acid leading to γ,δ-vicinal diols with double inversion of the configuration
Hirai, Atsushi,Yu, Xiao-Qiang,Tonooka, Terumichi,Miyashita, Masaaki
, p. 2482 - 2483 (2007/10/03)
A palladium-catalyzed stereospecific epoxide-opening reaction of γ,δ-epoxy-α,β-unsaturated esters with an alkylboronic acid leading to γ,δ-vicinal diols is described, which proceeds with retention of the configuration, i.e., via two consecutive SN/s
A study on the chelation control in the regioselective opening of 2,3-bifunctionalized epoxides
Righi, Giuliana,Pescatore, Giovanna,Bonadies, Francesco,Bonini, Carlo
, p. 5649 - 5656 (2007/10/03)
The results obtained in the MgBr2-mediated opening of 2,3-bifunctionalized epoxides are reported. The studies showed that the chelation control of MgBr2 between different functionalities can in some cases be selective.
Aminolysis of vinyl epoxides as an efficient entry to N-H vinylaziridines
Lindstroem, Ulf M.,Somfai, Peter
, p. 109 - 117 (2007/10/03)
Vinyl epoxides 8a-f 11 and 12 have been prepared from the corresponding epoxy alcohols while 8g was formed by a regioselective epoxidation of the parent diene. Aminolysis of these materials resulted in a regio- and stereoselective nucleophilic opening at C3 in good yields except for the sterically hindered substrates. The trans-oxiranes gave the anti-amino alcohols while the cis derivative 12 gave the syn isomer 17. Cyclization of the anti-amino alcohols was best effected using the Mitsunobu protocol giving the corresponding N-H vinylaziridines in 50-54% yields, while the syn-amino alcohol 17 was transformed into the cis-vinylaziridine 31 with chlorosulfonic acid followed by base treatment in 20% yield. The outcome of these cyclizations seems to indicate that they are controlled by subtle steric effects in the substrate. The N-H vinylaziridine 24 was alkylated with tert-butyl bromoacetate and the product subjected to an aza[2,3]-Wittig rearrangement to give tetrahydropyridine 30 while acetylation of 24 followed by base treatment resulted in an aza-[3,3]-Claisen rearrangement yielding the seven-membered lactam 32.
