131454-22-3Relevant academic research and scientific papers
Oxidative Sulfonylation of Hydrazones Enabled by Synergistic Copper/Silver Catalysis
Xu, Jun,Shen, Chao,Qin, Xian,Wu, Jie,Zhang, Pengfei,Liu, Xiaogang
, p. 3706 - 3720 (2021/02/05)
A copper/silver-cocatalyzed protocol for oxidative sulfonylation of hydrazones is demonstrated. A wide range of β-ketosulfones and N-acylsulfonamides are directly synthesized in moderate to good yields. Our work provides a viable method for scalable preparation of β-ketosulfone derivatives that have found wide applications in the pharmaceutical industry.
Chemoselective mono halogenation of β-keto-sulfones using potassium halide and hydrogen peroxide; synthesis of halomethyl sulfones and dihalomethyl sulfones
Suryakiran,Prabhakar,Srikanth Reddy,Chinni Mahesh,Rajesh,Venkateswarlu
, p. 877 - 881 (2007/10/03)
The synthesis of α-halo β-keto-sulfones using potassium halide and hydrogen peroxide as a chemoselective mono halogenation reagent and the synthesis of α,α-symmetrical and asymmetrical dihalo β-keto-sulfones and α-halo, α-alkyl and β-keto-sulfones is described. Base induced cleavage of α-halo β-keto-sulfones, α,α-dihalo β-keto-sulfones, and α-halo, α-alkyl β-keto-sulfones afforded the corresponding halomethyl sulfones, dihalomethyl sulfones and haloalkyl sulfones.
Efficient Diastereoselective Syntheses of erythro- Or threo-a-Alkyl-β-hydroxy Sulfones by Reductions of α-Alkyl-β-keto Sulfones with TiCI4/BHg or LiEtsBH/CeCl3, Respectively
Marcantoni, Enrico,Cingolani, Simone,Bartoli, Giuseppe,Bosco, Marcella,Sambri, Letizia
, p. 3624 - 3630 (2007/10/03)
A stereoselective synthesis of erythro- and threo-α-alkyl-β-hydroxy sulfones by reduction of the corresponding α-alkyl-β-keto sulfones has been developed. The pivotal role in this methodology is played by the chelating or nonchelating properties of the Lewis acid employed. The strong chelating TiCl4 led to the erythro isomer in high diastereomeric excess in noncoordinating solvents (CH2Cl2) at -78 °C using BH3/py as reducing agent, while the nonchelating CeCl3 gave a high excess of the threo isomer in coordinating solvents (THF) at the same temperature using lithium triethylborohydride (LiEt3BH) as reducing agent. Moreover, this methodology has been successfully utilized for the synthesis of α-allyl-β-hydroxy sulfones, which are useful synthetic intermediates to obtain 2,5-disubstituted tetrahydrofurans by electrophilic cyclization.
Steric effects in the diastereoselective reduction of β-ketosulfones
Grossert, J. Stuart,Dharmaratne, H. Ranjith W.,Cameron, T. Stanley,Vincent, Beverly R.
, p. 2860 - 2869 (2007/10/02)
The stereochemical course of the reduction of ketones adjacent to a chiral center normally shows some diastereoselectivity (described by Cram's rule), the degree of which is dependent on the structure of the ketone and on the reaction conditions; the selectivity in acyclic species is often not very great.In this paper, we described the sodium borohydride reduction of four acyclic β-ketosulfones, containing a chiral center at the α-position, in which the products are formed with high diastereoselectivity.Reasons for this selectivity became apparent when we were able to show that these ketosulfones apparently exist predominantly in the same conformation in solution as in the solid state.This conformation requires that the preferred trajectory for nucleophilic attack on the carbonyl group leads to reaction on the re face, to yield the threo diastereomer of the β-hydroxysulfone.The results that led to these conclusions were obtained from stuctural studies by X-ray crystallography, as well as by detailed 1H and 13C nuclear magnetic resonance spectroscopy.In some cases, the latter spectra were run both in solution and in the solid state.
