133957-57-0Relevant articles and documents
Enantioselective Conjugate Azidation of α,β-Unsaturated Ketones under Bifunctional Organocatalysis by Direct Activation of TMSN3
Humbrías-Martín, Jorge,Pérez-Aguilar, M. Carmen,Mas-Ballesté, Rubén,Dentoni Litta, Antonella,Lattanzi, Alessandra,Della Sala, Giorgio,Fernández-Salas, Jose A.,Alemán, José
, p. 4790 - 4796 (2019)
An enantioselective organocatalytic conjugate azidation of α,β-unsaturated ketones is presented. A bifunctional organocatalyst activates TMSN3, triggering the nucleophilic addition of the azido group to enones in absence of external promoters and avoiding the direct use or the pre-formation of highly toxic and explosive hydrazoic acid. This protocol proceeds with excellent enantiocontrol under mild conditions. DFT calculations and mechanistic trials have been performed in order to demonstrate the direct activation performed by the bifunctional organocatalyst. (Figure presented.).
Parallel recognition by virtue of differentiation between carbonyls, acetals and enones
Chen, Jian-Xie,Sakamoto, Katsumasa,Orita, Akihiro,Otera, Junzo
, p. 8411 - 8420 (1998)
'Parallel recognition', a new concept for compacting synthetic processes in which different transformations are performed simultaneously on separate reaction sites, has been advance. Ketones/α,β-enones and aldehydes/acetals are able to react selectively w
FeCl3·6H2O-catalyzed mukaiyama-aldol type reactions of enolizable aldehydes and acetals
Rodríguez-Gimeno, Alejandra,Cuenca, Ana B.,Gil-Tomás, Jesús,Medio-Simón, Mercedes,Olmos, Andrea,Asensio, Gregorio
, p. 8263 - 8270 (2015/03/18)
Mukaiyama-aldol type reactions of acetals derived from enolizable aldehydes with FeCl3·6H2O, an eco-friendly, low-cost, and stable catalyst, lead to β-methoxycarbonyl compounds with nearly quantitative yields. The methodology is extended to the parent aldehydes as starting materials, leading to the corresponding aldols with lower yields, but efficiently. Different alkyl and aryl substituted acetals and aldehydes have been tested in the reaction with linear and cyclic silyl enol ethers. Reactions are carried out in an open air atmosphere, and additives are not required. Acetals can be considered activating groups of the carbonyl moiety rather than a protecting group in this type of FeCl3·6H2O-catalyzed condensation.
Synthesis and structure of an extremely air-stable binuclear hafnocene perfluorooctanesulfonate complex and its use in lewis acid-catalyzed reactions
Qiu, Renhua,Zhang, Guoping,Zhu, Yuyang,Xu, Xinhua,Shao, Lingling,Li, Yinhui,An, Delie,Yin, Shuangfeng
supporting information; scheme or table, p. 6488 - 6494 (2010/02/28)
An extremely air-stable μ2-hydroxy-bridged binuclear hafonocene perfluorooctanesulfoante complex was successfully synthesized. This complex showed high catalytic efficiency in the esterification of alcohols, phenol, thiol, and amines, in the Friedel-Crafts acylation of alylaryl ethers, in the Mukaiyama aldol reaction, and in the allylation of aldehydes and could be reused.
Tin-mediated organic reactions: A practical method for the synthesis of β-hydroxynitriles and β-hydroxyketones
Sun, Peipei,Shi, Baochuan
, p. 318 - 319 (2007/10/03)
In the presence of chlorotrimethylsilane, the tin mediated addition of bromoacetonitrile or α-bromacetophenone to aldehydes in THF gives β- hydroxynitriles or β-hydroxyketones in moderate to good yields.
Samarium(II) diiodide-mediated intermolecular aldol type reactions of phenacyl bromides with carbonyl compounds
Aoyagi, Yutaka,Yoshimura, Mizue,Tsuda, Masako,Tsuchibuchi, Tomomasa,Kawamata, Saori,et al.
, p. 689 - 692 (2007/10/02)
Intermolecular aldol type reactions of phenacyl bromides with various carbonyl compounds mediated by samarium(II) diiodide afford β-hydroxy ketones in moderate to good yields.The addition of N,N,N',N'-tetramethylethylenediamine or diethylaluminium chlorid
Indium-Induced Reaction of Phenacyl Iodide. Deiodinative Dimerization to β,γ-Epoxy Ketone and Aldol Condensation with Aldehydes
Araki, Shuki,Butsugan, Yasuo
, p. 727 - 729 (2007/10/02)
The reaction of phenacyl iodide with indium metal gave 3,4-epoxy-1,3-diphenyl-1-butanone which, on treatment with silica gel, gave 2,4-diphenylfuran and 2,4-diphenyl-4-oxobutanal.Metallic indium as well as indium(I) iodide were found to mediate the aldol condensation between α-halo ketone and aldehyde.