A Versatile Synthesis of Various Substituted Taurines from Vicinal Amino Alcohols and Aziridines

Abstract

Taurine and structurally diverse substituted taurines have been synthesized by peroxyformic acid oxidation of the thiazolidine-2-thione intermediates generated from vicinal amino alcohols or aziridines and carbon disulfide. The stereochemistry and mechanisms of the reactions are dis-

Highly effective CS2 conversion with aziridines catalyzed by novel [Dy24] nano-cages in MOFs under mild conditions

“…Notably, because of the high stability of the p–π conjugation in intermediate III by a S N 2 nucleophilic process, CS 2 preferentially attacked the benzylic carbon atom to form the single product of 5-substituted thiazolidine-2-thione. 42 In addition, the single-crystal of 3-ethyl-5-phenylthiazolidine-2-thione was obtained and resolved (Table S5 and Fig. S13, ESI†), further confirming the method of production.…”

Expeditious Synthesis of Dianionic-Headed 4-Sulfoalkanoic Acid Surfactants

“…Through the previously mentioned oxidation procedure with peroxyformic acid [ 18 , 19 , 20 ], all xanthates 3 were converted into the corresponding 4-sulfoalkanoic acids 4 in almost quantitative yields. Under the current acidic oxidation conditions, the xanthate group was oxidized into sulfonic acid and the methyl-carboxylate group in xanthates 3 was hydrolyzed into the carboxylic acid group ( Supplementary materials ) ( Table 2 and Scheme 3 ).…”

“…We previously prepared taurine and homotaurine derivatives by oxidation of thioacetates [ 21 , 22 , 23 , 24 , 25 ] and xanthates [ 18 , 19 , 20 ]. Douglass and his coworkers reported that xanthates (ROCS 2 R’) were chlorinated into alkoxydichloromethanesulfenyl chlorides (ROCCl 2 SCl) and alkylsulfur trichlorides (R’SCl 3 ) with chlorine under anhydrous conditions [ 26 , 27 ].…”

Synthesis of sulfonopeptides

“…Thus, there are structurally diverse 2-aminoalkanesulfonic acids, including α-substituted taurines, 9-19 β-substituted taurines, 15,[18][19][20][21][22][23][24][25][26][27] α,α- 28,29 and β,β-disubstituted taurines, 18,27,29,30 cis-and trans-α,β-disubstituted taurines. 31,32 These results in abundant structural diversity of sulfonopeptides in comparison with native peptides.…”