13129-38-9Relevant articles and documents
Metal-free synthesis of biaryls from aryl sulfoxides and sulfonanilides via sigmatropic rearrangement
Yoshida, Akira,Okamoto, Koichi,Yanagi, Tomoyuki,Nogi, Keisuke,Yorimitsu, Hideki
, (2020/05/20)
Treatment of aryl sulfoxides and sulfonanilides with trifluoroacetic anhydride resulted in the dehydrative metal-free construction of the corresponding unsymmetrical biaryls. The reaction would proceed via (1) the activation of aryl sulfoxide with the anhydride, (2) interrupted Pummerer reaction of the resulting arylsulfonium with sulfonanilide, (3) [3,3] sigmatropic rearrangement to cleave the transient S–N bond and to form the prospective biaryl C–C bond, and (4) global aromatization. The choice of the amino protecting group is crucial, and only N-sulfonylanilines, i.e., sulfonanilides, could participate in the formation of biaryls.
Structure-activity relationship (SAR) of the α-amino acid residue of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists
Zhong, Min,Hanan, Emily J.,Shen, Wang,Bui, Minna,Arkin, Michelle R.,Barr, Kenneth J.,Evanchik, Marc J.,Hoch, Ute,Hyde, Jennifer,Martell, Jose R.,Oslob, Johan D.,Paulvannan, Kumar,Prabhu, Saileta,Silverman, Jeffrey A.,Wright, Jasmin,Yu, Chul H.,Zhu, Jiang,Flanagan, W. Mike
scheme or table, p. 307 - 310 (2011/02/27)
This letter describes the structure-activity relationship (SAR) of the 'right-wing' α-amino acid residue of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists. Novel (S)-substituted heteroaryl-bearing α-amino acids have been identified
Biotransformation of organic sulfides. Part 12. Conversion of heterocyclic sulfides to chiral sulfoxides by Helminthosporium sp. NRRL 4671 and Mortierella isabellina ATCC 42613
Holland, Herbert L.,Turner, Carl D.,Andreana, Peter R.,Nguyen, Doan
, p. 463 - 471 (2007/10/03)
The enantioselective oxidation of a series of heterocyclic prochiral sulfides to chiral sulfoxides has been examined using the fungal biocatalysts Helminthosporium species NRRL 4671 and Mortierella isabellina ATCC 42613. Methylthiofuranyl and -thiophenyl