131252-66-9Relevant academic research and scientific papers
Coupling reaction of vinyl halides with ketones or aldehydes mediated by samarium diiodide
Kunishima, Munetaka,Yoshimura, Kazuma,Nakata, Daisuke,Hioki, Kazuhito,Tani, Shohei
, p. 1196 - 1197 (1999)
The Barbier- or Grignard-type reaction of vinyl iodides with ketones or aldehydes proceeds on treatment with samarium diiodide in benzene containing hexamethylphosphoric triamide (HMPA) to afford the corresponding coupling compounds (allyl alcohols). The reaction was shown to involve vinyl samariums as an intermediate.
Cobalt-Catalyzed Asymmetric 1,4-Hydroboration of Enones with HBpin
Ren, Xiang,Lu, Zhan
, p. 8370 - 8374 (2021/11/01)
Herein, a series of new 8-OIQ cobalt complexes were synthesized and used for cobalt-catalyzed chemo- and enantioselective 1,4-hydroboration of enones with HBpin to access chiral β,β-disubstituted ketones with good to excellent chemo- and enantioselectivties. This protocol is operationally simple and shows a broad substrate scope.
Br?nsted Base-Catalyzed Transformation of α,β-Epoxyketones Utilizing [1,2]-Phospha-Brook Rearrangement for the Synthesis of Allylic Alcohols Having a Tetrasubstituted Alkene Moiety
Kondoh, Azusa,Tasato, Naoko,Aoki, Takuma,Terada, Masahiro
, p. 5170 - 5175 (2020/07/04)
A stereoselective transformation of α,β-epoxyketones into alkenylphosphates having a hydroxymethyl group on the β-carbon was established by utilizing the [1,2]-phospha-Brook rearrangement under Br?nsted base catalysis. The reaction involves the catalytic generation of an α-oxygenated carbanion located at the α-position of an epoxide moiety through the [1,2]-phospha-Brook rearrangement and the following epoxide opening. Further transformation of the alkenylphosphates by the palladium-catalyzed cross-coupling reaction with Grignard reagents provided allylic alcohols having a stereodefined all-carbon tetrasubstituted alkene moiety.
Base-promoted isomerization of CF3-containing allylic alcohols to the corresponding saturated ketones under metal-free conditions
Hamada, Yoko,Kawasaki-Takasuka, Tomoko,Yamazaki, Takashi
supporting information, p. 1507 - 1512 (2017/08/14)
Following to the computational expectation, our previously reported intriguing 1,3-proton shift of 4,4,4-trifluorobut-2-yn-1-ols was successfully extended to the 4,4,4-trifluorobut-2-en-1-ol system under metal-free conditions to afford the corresponding saturated ketones in high to excellent chemical yields using such a convenient and easy-to-handle base as DBU at the toluene refluxing temperature, and utilization of the corresponding optically active substrates unambiguously demonstrated that this transformation proceeded in a highly stereoselective fashion.
Synthesis and antimalarial activity of 3,3-spiroanellated 5,6-disubstituted 1,2,4-trioxanes
Maurya, Ranjani,Soni, Awakash,Anand, Devireddy,Ravi, Makthala,Raju, Kanumuri S.R.,Taneja, Isha,Naikade, Niraj K.,Puri,Wahajuddin,Kanojiya, Sanjeev,Yadav, Prem P.
, p. 165 - 169 (2013/03/29)
Novel 3,3-spiroanellated 5-aryl, 6-arylvinyl-substituted 1,2,4-trioxanes 19-34 have been synthesized and appraised for their antimalarial activity against multidrug-resistant Plasmodium yoelii nigeriensis in Swiss mice by oral route at doses ranging from 96 mg/kg × 4 days to 24 mg/kg × 4 days. The most active compound of the series (compound 25) provided 100% protection at 24 mg/kg × 4 days, and other 1,2,4-trioxanes 22, 26, 27, and 30 also showed promising activity. In this model, β-arteether provided 100 and 20% protection at 48 mg/kg × 4 days and 24 mg/kg × 4 days, respectively, by oral route. Compound 25 displayed a similar in vitro pharmacokinetic profile to that of reference drug β-arteether. The activity results demonstrated the importance of an aryl moiety at the C-5 position on the 1,2,4-trioxane pharmacophore.
The epoxy-Ramberg-Baecklund reaction (ERBR): A sulfone-based method for the synthesis of allylic alcohols
Evans, Paul,Johnson, Paul,Taylor, Richard J. K.
, p. 1740 - 1754 (2007/10/03)
The epoxy-Ramberg-Baecklund reaction (ERBR) is outlined, in which α,β-epoxy sulfones are converted into a range of mono-, di- and tri-substituted allylic alcohols, on treatment with base. Modification of this method enabled the preparation of enantio-enriched allylic alcohols following the diastereoselective epoxidation of enantio-enriched vinyl sulfones that were accessed efficiently from the chiral pool. The scope, optimisation and limitations of the ERBR as a method for the preparation of allylic alcohols are discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
