256474-26-7Relevant academic research and scientific papers
Chemo-enzymatic synthesis of (R)- and (S)-3,4-dichlorophenylbutanolide intermediate in the synthesis of sertraline
Barbieri, Cinzia,Caruso, Enrico,D'Arrigo, Paola,Pedrocchi Fantoni, Giuseppe,Servi, Stefano
, p. 3931 - 3937 (1999)
3,4-Dichlorophenacylchloride was reduced with whole cell biocatalysts to give the (R)- or (S)-chlorohydrine in high yields and good to high enantiomeric excess. Yields and enantiomeric purity of the (S)-enantiomer were increased to 95 and >98%, respective
Biomimetic non-heme iron-catalyzed epoxidation of challenging terminal alkenes using aqueous H2O2 as an environmentally friendly oxidant
Fingerhut, Anja,Vargas-Caporali, Jorge,Leyva-Ramírez, Marco Antonio,Juaristi, Eusebio,Tsogoeva, Svetlana B.
, (2019/09/06)
Catalysis mediated by iron complexes is emerging as an eco-friendly and inexpensive option in comparison to traditional metal catalysis. The epoxidation of alkenes constitutes an attractive application of iron(III) catalysis, in which terminal olefins are challenging substrates. Herein, we describe our study on the design of biomimetic non-heme ligands for the in situ generation of iron(III) complexes and their evaluation as potential catalysts in epoxidation of terminal olefins. Since it is well-known that active sites of oxidases might involve imidazole fragment of histidine, various simple imidazole derivatives (seven compounds) were initially evaluated in order to find the best reaction conditions and to develop, subsequently, more elaborated amino acid-derived peptide-like chiral ligands (10 derivatives) for enantioselective epoxidations.
One-pot route to β-adrenergic blockers via enantioselective organocatalysed epoxidation of terminal alkenes as a key step
Held, Felix E.,Wei, Shengwei,Eder, Kathrin,Tsogoeva, Svetlana B.
, p. 32796 - 32801 (2014/08/18)
A convenient and environmentally attractive one-pot two-step process for the synthesis of β-adrenergic blockers via Shi's organocatalytic epoxidation of terminal alkenes and subsequent aminolysis reaction of epoxides with isopropylamine under mild reaction conditions has been developed. This journal is the Partner Organisations 2014.
Asymmetric synthesis of β-adrenergic blockers through multistep one-pot transformations involving in situ chiral organocatalyst formation
Wei, Shengwei,Messerer, Regina,Tsogoeva, Svetlana B.
supporting information; experimental part, p. 14380 - 14384 (2012/02/01)
Two birds one stone: A new atom-economical one-pot approach to enantioselective chiral drug synthesis, involving in situ multistep organocatalyst formation and the application of the reaction for multistep sequential synthesis of β-adrenergic blockers is disclosed (see scheme).
Effective asymmetric epoxidation of styrenes by chiral dioxirane
Goeddel, David,Shu, Lianhe,Yuan, Yi,Wong, O. Andrea,Wang, Bin,Shi, Yian
, p. 1715 - 1717 (2007/10/03)
High enantioselectivity (80-92% enantiomeric excess (ee)) has been obtained for the epoxidation of various styrenes using an easily prepared ketone (4) catalyst.
Convenient synthesis of optically active 1,2-diol monosulfonates and terminal epoxides via oxazaborolidine-catalyzed asymmetric borane reduction of α-sulfonyloxy ketones
Cho, Byung Tae,Yang, Weon Ki,Choi, Ok Kyung
, p. 1204 - 1211 (2007/10/03)
A very convenient asymmetric synthesis of 1,2-diol monosulfonates and terminal epoxides with high optical purity via oxazaborolidine-catalyzed asymmetric borane reduction of α-sulfonyloxy ketones using N-ethyl-N-isopropylaniline-borane complex as borane carrier has been developed.
A two-step asymmetric synthesis of (R)-monoaryl epoxides using a chiral oxathiane as a recoverable reagent: Application to the preparation of (R)-β-adrenergic compounds
Solladie-Cavallo,Diep-Vohuule
, p. 3494 - 3498 (2007/10/02)
It is shown that chiral oxathiane 1 is a recoverable and efficient chiral auxiliary which provides, in two steps, (R)-monoaryl epoxides in high enantiomeric purity (98% R and 92% R according to the solvent used). (R)-β-Adrenergic compounds (R)-(-)-DCI and
