21504-07-4Relevant academic research and scientific papers
Difunctionalization of Alkynones by Base-Mediated Reaction with α,α-Dithioketones
Yang, Yajie,Cheng, Lu,Wang, Mengdan,Yin, Liqiang,Feng, Ye,Wang, Chengyu,Li, Yanzhong
, p. 5339 - 5343 (2021)
A novel 1,2-difunctionalization of alkynones via an umpolung strategy for the synthesis of tetrasubstituted olefins has been developed. This procedure is realized by a formal C-C σ-bond cleavage reaction of cyclic α,α-dithioketones and subsequent deprotection. Notable features of this approach include excellent yields, mild reaction conditions, a broad substrate scope, and operational simplicity.
Substituted α-Sulfur Methyl Carbanions: Effective Homologating Agents for the Chemoselective Preparation of β-Oxo Thioethers from Weinreb Amides
Senatore, Raffaele,Ielo, Laura,Urban, Ernst,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 2466 - 2470 (2018/05/03)
The proper generation of α-thiomethyllithium reagents via reductive lithiation or deprotonation followed by reaction with variously functionalized Weinreb amides represents an excellent method to access β-oxo thioethers. The procedure is adaptable to alky
1,3-Dithianes as Acyl Anion Equivalents in Pd-Catalyzed Asymmetric Allylic Substitution
Yao, Kun,Liu, Delong,Yuan, Qianjia,Imamoto, Tsuneo,Liu, Yangang,Zhang, Wanbin
supporting information, p. 6296 - 6299 (2016/12/23)
A Pd-catalyzed asymmetric allylic substitution with 1,3-dithianes as acyl anion equivalents has been developed in high yields and excellent enantioselectivities. The reaction was performed on a gram scale, and the corresponding alkylated products were con
Weinreb amide based building blocks for convenient access to 1,1-diarylethenes and isocombretastatin analogues
Balasubramaniam, Sivaraman,Kommidi, Harikrishna,Aidhen, Indrapal Singh
supporting information; experimental part, p. 2683 - 2686 (2011/06/19)
A successful strategy based on the synthetic equivalent containing Weinreb amide functionality for the convenient access to 1,1-diarylethenes in general and for the isocombretastatin analogues in particular has been developed from the commercially available glyoxalic acid. The convenience with which the structural variations can be made in assembling the aryl residues shows generality associated with the developed strategy. The intermediates also provide access to 1,2,2-triarylethanones, represented by the synthesis of advanced intermediate of tamoxifen.
A new synthesis of 2-substituted-1,3-dithianes from trichloromethyl compounds
Rivera, Nancy González,Becerril, David Corona,Guadarrama-Pérez, Carlos,Covarrubias-Zu?iga, Adrian,Avila-Zárraga, José Gustavo,Romero-Ortega, Moisés
, p. 1201 - 1204 (2007/10/03)
Trichloromethyl compounds are efficiently converted into 1,3-dithianes upon reaction with a disodium 1,3-propanedithiolate-1,3-propanedithiol mixture in DMF solution at 0 °C. This synthesis is limited to those substrates where the substituent attached to the trichloromethyl group is an electron-withdrawing group.
Synthetic equivalents based on Weinreb amide functionality for convenient access to monoprotected α-diketones
Balasubramaniam, Sivaraman,Aidhen, Indrapal Singh
, p. 959 - 963 (2008/02/02)
A convenient new strategy for the synthesis of monoprotected α-diketones has been achieved. The strategy is based on the use of hitherto unreported N-methoxy-N-methyl-1,3-dithiolane-2-carboxamide and N-methoxy-N-methyl-1,3-dithiane-2-carboxamide as synthe
Enantioselective preparation of 2-substituted-1,3-dithiane 1-oxides using modified Sharpless sulphoxidation procedures
Page, Philip C. Bulman,Wilkes, Robin D.,Namwindwa, Ernest S.,Witty, Michael J.
, p. 2125 - 2154 (2007/10/03)
Enantioselective sulphoxidation of a wide range of 2-substituted-1,3-diathianes has been carried out using modified Sharpless conditions to furnish the corresponding sulphoxides in optically enriched form. Deacylation of 2-acyl-1,3-dithiane 1-oxide deriva
Direct Ni° mediated synthesis of ketones from acyl bromides and Grignard reagents
Malanga, Corrado,Aronica, Laura A.,Lardicci, Luciano
, p. 9185 - 9188 (2007/10/02)
A catalytic amount of NidppeCl2 converts an acyl bromide directly into ketones at 0°C in THF in the presence of a Grignard reagent. The described procedure represents a useful way to afford dialkyl, diaryl or alkyl aryl ketones as well as 1,2-diketones. In the adopted reaction conditions double bonds, esters and ketones are unaffected.
Lewis acid mediated addition of 2-acyl-1,3-dithianes to α,β-unsaturated ketones: Synthesis of cyclohexenedione mono-dithioacetals
Bulman Page, Philip C.,Marchington, Allan P.,Graham, Lisa J.,Harkin, Shaun A.,Wood, William W.
, p. 10369 - 10386 (2007/10/02)
2-Acyl-1,3-dithianes undergo Lewis acid-mediated conjugate addition to α,β-unsaturated ketones to provide 1,5-diketones which suffer base-catalyzed intramolecular aldol reaction to produce monodithioacetals of cyclohex-2-en-1,4-diones and cyclohex-3-en-1,
SUBSTITUTION REACTIONS WITH ORGANOALUMINUM COMPOUNDS. VIII. A NEW VERSION OF THE SYNTHESIS OF 2-ACYL-1,3-DITHIANES
Tolstikov, G. A.,Spivak, A. Yu.,Kresteleva, I. V.,Vyrypaev, E. M.
, p. 2111 - 2116 (2007/10/02)
The reaction of 2-alumino-1,3-dithianes with acyl chlorides takes place in competing C- and S-acylation directions, the ratio of which depends substantially on the structure of the reagents.The C-acylation is a new version of the synthesis of 2-acyl-1,3-d
