147255-16-1Relevant academic research and scientific papers
A step-wise reduction of nonracemic α-ketoamides to α-methine amides under mild conditions
Wang, Bing,Wang, Min,Jia, Tao,Lou, Yazhou,Liao, Jian,Cao, Peng
, p. 2042 - 2047 (2016/04/05)
A step-wise reductive method that converts nonracemic γ-chiral α-ketoamides into amide derivatives was developed under mild conditions. The method involves a highly efficient three-step transformation including NaBH4-reduction, bromination and Pd/C hydrogenation reactions. As a consequence, a variety of nonracemic γ-diaryl amides products were obtained in high overall yields with excellent enantiomeric specificity. The utility of the method is demonstrated through the concise formal synthesis of (+)-sertraline in good overall yield.
Rhodium-catalyzed asymmetric arylation of β,γ-unsaturated α-ketoamides for the construction of nonracemic γ,γ- diarylcarbonyl compounds
Wang, Juanjuan,Wang, Min,Cao, Peng,Jiang, Liyin,Chen, Guihua,Liao, Jian
, p. 6673 - 6677 (2014/07/08)
A highly regio- and enantioselective rhodium-catalyzed 1,4-addition of arylboronic acids to β,γ-unsaturated α-ketoamides using a simple new chiral sulfinylphosphine ligand is described. This transformation provides an attractive approach to construct chiral nonracemic γ,γ-diarylsubstituted carbonyl compounds, as exemplified in the concise syntheses of sertraline and tetrahydroquinoline-2-carboxylamide. Constructing chiral carbonyls: A simple new chiral sulfinylphosphine ligand L was developed, which promoted excellent 1,4-selectivities and enantioselectivities in the rhodium-catalyzed conjugate addition of arylboronic acids to β,γ-unsaturated α-ketoamides. The desired γ,γ-diaryl-α-ketocarbonyl compounds were afforded with high yields and high optical purities.
Enantioselective syntheses of (+)-sertraline and (+)-indatraline using lithiation/borylation-protodeboronation methodology
Roesner, Stefan,Casatejada, Javier Mansilla,Elford, Tim G.,Sonawane, Ravindra P.,Aggarwal, Varinder K.
supporting information; experimental part, p. 5740 - 5743 (2011/12/22)
The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCl, H2O), or a solvent switch to CHCl3, to achieve high yields and high selectivities.
Palladium-catalyzed γ-selective and stereospecific allyl-aryl coupling between acyclic allylic esters and arylboronic acids
Ohmiya, Hirohisa,Makida, Yusuke,Li, Dong,Tanabe, Masahito,Sawamura, Masaya
supporting information; experimental part, p. 879 - 889 (2010/03/25)
Reactions between acyclic (E)-allylic acetates and arylboronic acids in the presence of a palladium catalyst prepared from Pd(OAc)2, phenanthroline (or bipyridine), and AgSbF6 (1:1.2:1) proceeded with excellent γ-selectivity to afford allyl-aryl coupling products with E-configuration. The reactions of α-chiral allylic acetates took place with excellent α-to-γ chirality transfer with syn stereochemistry to give allylated arenes with a stereogenic center at the benzylic position. The reaction tolerated a broad range of functional groups in both the allylic acetates and the arylboronic acids. Furthermore, γ-arylation of cinnamyl alcohol derivatives afforded gem-diarylalkane derivatives containing an unconjugated alkenic substituent. The synthetic utility of this method was demonstrated by its utilization in an efficient synthesis of (+)-sertraline, an antidepressant agent. The observed γ-regioselectivity and E-1,3-syn stereochemistry were rationalized based on a Pd(II) mechanism involving transmetalation between a cationic mono(acyloxo)palladium(II) complex and arylboronic acid, and directed carbopalladation followed by syn-β-acyloxy elimination. The results of stoichiometric reactions of palladium complexes related to possible intermediates were fully consistent with the proposed mechanism.
Asymmetric hydrogenation of a 4,4-diaryl-3-butenoate; a novel approach to sertraline.
Boulton, Lee T,Lennon, Ian C,McCague, Raymond
, p. 1094 - 1096 (2007/10/03)
The asymmetric hydrogenation of a selectively crystallised (E)-4,4-diaryl-3-butenoate with a rhodium-PhanePhos catalyst is described, providing an intermediate to the antidepressant sertraline.
Catalytic asymmetric synthesis of diarylacetates and 4,4-diarylbutanoates. A formal asymmetric synthesis of (+)-sertraline
Davies, Huw M. L.,Stafford, Douglas G.,Hansen, Tore
, p. 233 - 236 (2008/02/12)
(equation presented) The intermolecular C-H insertion chemistry of phenyldiazoacetates catalyzed by dirhodium tetrakis((S)-N-(dodecylbenzenesulfonyl)prolinate) (Rh2(S-DOSP)4) can be effectively carried out on cyclohexadienes, leading to the asymmetric synthesis of diarylacetates. The reaction of vinyldiazoacetates with cyclohexadienes results in an unprecedented carbenoid reaction that is formally a combined C-H insertion/Cope rearrangement. The synthetic utility of this novel transformation was demonstrated by its utilization in a formal asymmetric synthesis of (+)-sertraline.
A Catalytic Enantioselective Synthetic Route to the Important Antidepressant Sertraline
Corey, E. J.,Gant, Thomas, G.
, p. 5373 - 5376 (2007/10/02)
An efficient catalytic enantioselective synthesis of the important antidepressant sertraline is described.
Synthesis of 4(S)-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone by SN2 cuprate displacement of an activated chiral benzylic alcohol
Quallich,Woodall
, p. 10239 - 10248 (2007/10/02)
Two routes for the preparation of 4(S)-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone are reported. The most efficient route generates a chiral benzylic alcohol by catalytic asymmetric oxazaborolidine reduction of a γ-ketoester that is subsequently activated and displaced in an SN2 manner with a higher order cuprate. Intramolecular Friedel-Crafts cyclization of the resulting t-butylester affords the title compound.
