123191-68-4Relevant academic research and scientific papers
Facile synthesis of various substituted taurines, especially syn- and anti-1,2-disubstituted taurines, from nitroolefins
Chen, Ning,Xu, Jiaxi
, p. 2513 - 2522 (2012/04/11)
Taurine and substituted taurines present a group of important structural elements in many natural products. Various substituted taurines, including 1- and 2-substituted, 1,1-, syn-1,2-, and anti-1,2-disubstituted taurines, were synthesized from the corresponding nitroolefins via Michael addition with thioacetic acid, oxidation with peroxyformic acid, and the catalytic hydrogenation under the catalysis of palladium on carbon or platinum dioxide. It is a general, versatile, and salt-free method for the preparation of substituted taurines, especially for syn- and anti-1,2-disubstituted taurines and some taurines with more bulky substituents. The stereostructures of both syn- and anti-1,2-disubstituted taurines were deduced from the nitroalkyl thioacetates in the Michael addition, which were identified via the Karplus equation analysis and computational analysis, and finally confirmed by the XRD single crystal analysis. The diastereoselectivity in the Michael addition was rationalized with the Cram rule.
Amino-sulfonation of alkenes in a three-component reaction
Cordero, Franca M.,Cacciarini, Martina,Machetti, Fabrizio,De Sarlo, Francesco
, p. 1407 - 1411 (2007/10/03)
2-Aminoalkanesulfonic acids have been synthesized by a three-component alkene/SO3·-DMF/acetonitrile reaction, followed by hydrolysis. Trifluoromethanesulfonic acid was added to the amino-sulfonation mixture to accelerate the reaction and prevent the competitive formation of by-products. The reported two-step procedure provided a concise and versatile approach to new analogues of the natural amino acid taurine. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
