128574-71-0Relevant academic research and scientific papers
Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts
Fujii, Kazuki,Mitsudo, Koichi,Mandai, Hiroki,Suga, Seiji
supporting information, p. 2778 - 2788 (2017/08/23)
An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).
Copper-catalyzed double intramolecular ullmann coupling for the synthesis of diastereomerically and enantiomerically pure 4b,9b-dihydrobenzofuro[3,2-b]benzofurans
Imrich, Hans-Georg,Conrad, Jürgen,Beifuss, Uwe
, p. 7718 - 7734 (2015/12/31)
The copper-catalyzed double intramolecular Ullmann coupling of syn-1,2-bis(2-bromoaryl)ethane-1,2-diols with catalytic amounts of CuII oxinate as the copper source, K3PO4 as a base, and KI as a reductant in aqueous acetoni
Selective Pinacol Coupling on Regeneratable Supported Acids in Sole Water
Sotto, Nicolas,Billamboz, Muriel,Chevrin-Villette, Carole,Len, Christophe
, p. 6375 - 6380 (2015/06/30)
Efficient pinacol coupling was developed in sole water, using a reusable heterogeneous supported acid source and zinc as cheap available metal source. This medium can be easily regenerated up to 10-fold without loss of activity. Moreover, supported acids enhance the selectivity of the pinacol coupling reaction compared with homogeneous acids.
Straightforward access to chiral diol bidentate ligands: Their efficient enantioselective induction in the addition of diethylzinc to aromatic aldehydes
G?k, Yaar,Külolu, Soner,G?k, Halil Zeki,Kekec, Levent
, p. 835 - 838 (2015/02/19)
Enantiopure C2-symmetric diol bidentate ligands have been synthesized in a straightforward manner through a three-step reaction with good yields. The synthesized C2-symmetric diol bidentate ligands were used in the addition of diethylzinc to various aromatic aldehydes, a general catalytic benchmark reaction, in order to assess their enantioselective induction properties. The enantioselective addition of diethylzinc to 1-naphthaldehyde and 3-chlorobenzaldehyde was achieved with an enantiomeric excess (ee) of up to 98%. All synthesized ligands were also evaluated in the addition of diethyzinc to aromatic aldehydes including an extra metal such as Ti(IV) (up to 99% ee).
Straightforward access to chiral diol bidentate ligands: Their efficient enantioselective induction in the addition of diethylzinc to aromatic aldehydes
G?k, Ya?ar,Küloglu, Soner,G?k, Halil Zeki,Kekec?, Levent
, p. 835 - 838 (2015/04/16)
Enantiopure C2-symmetric diol bidentate ligands have been synthesized in a straightforward manner through a three-step reaction with good yields. The synthesized C2-symmetric diol bidentate ligands were used in the addition of diethylzinc to various aromatic aldehydes, a general catalytic benchmark reaction, in order to assess their enantioselective induction properties. The enantioselective addition of diethylzinc to 1-naphthaldehyde and 3-chlorobenzaldehyde was achieved with an enantiomeric excess (ee) of up to 98%. All synthesized ligands were also evaluated in the addition of diethyzinc to aromatic aldehydes including an extra metal such as Ti(IV) (up to 99% ee).
Novel synthesis of pinacols and sulfones promoted by Smi£ NiCl2 bimetallic system
Ye, Yuyuan,Zhou, Qizhong,Zheng, Renhua,Jiang, Huajiang,Chen, Rener,Zhang, Yongmin
experimental part, p. 331 - 334 (2012/05/04)
Smi£NiCl2 as a reductive system promoted reductive coupling of aryl adehydes and aryl ketone into pinacols in good yields and also promoted coupling reaction of aryl sulfonyl chlorides and active halides into sulfones in good yields.
Bidirectional metalation of hydrobenzoin: Direct access to new chiral ligands and auxiliaries
Cho, Inhee,Meimetis, Labros,Britton, Robert
supporting information; experimental part, p. 1903 - 1906 (2009/09/30)
A bidirectional ortho metalation of the readily available chiral diol hydrobenzoin has been developed that provides direct access to new ortho-functionalized hydrobenzoin derivatives. This one-pot procedure should broaden the utility of hydrobenzoin as an
Enantioselective Preparation of Benzimidazole Derivatives and Their Salts
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Page/Page column 6, (2009/01/24)
The invention relates to a new process for preparing benzimidazole derivatives having a chiral sulfoxide group in enantiomerically pure form or in a form in which one of the two enantiomers is present in an increased quantity over the other enantiomer. The invention likewise relates to a process for preparing the salts of the individual enantiomers of the benzimidazole derivatives with a chiral sulfoxide group. The invention relates in particular to a process for preparing the S-enantiomer of omeprazole (also known as esomeprazole) and the salts thereof, more particularly the zinc salt of the S-enantiomer of omeprazole. In the new process a prochiral sulfide is oxidized in an organic solvent with an oxidizing agent in the presence of a titanium(IV) complex.
InCl3/Al mediated pinacol coupling reactions of aldehydes and?ketones in aqueous media
Wang, Chunyan,Pan, Yuanjiang,Wu, Anxin
, p. 429 - 434 (2007/10/03)
A systematic work on the homo-pinacol coupling reactions of benzophenones, aldehydes, and acetophenones in aqueous media with InCl3/Al is described for the first time, in which various 1,2-diols are obtained in moderate to good yields.
Synthesis and chemistry of enantiomerically pure 10,11-dihydrodibenzo[b,f] thiepines
Wyatt, Paul,Hudson, Andrew,Charmant, Jonathan,Orpen, A. Guy,Phetmung, Hirihattaya
, p. 2218 - 2232 (2008/02/04)
Several chiral thiepines were efficiently constructed using sulfur diimidazole in combination with a variety of bislithiated carbon fragments. The sulfur atom in these thiepines is found to be unusually unreactive compared to diphenylsulfide. The Royal Society of Chemistry 2006.
