872874-24-3Relevant academic research and scientific papers
NaClO2-mediated preparation of pyridine-2-sulfonyl chlorides and synthesis of chiral sulfonamides
Xu, Dong,Yang, Shiyi,Gao, Aijun,Yang, Zhanhui
, p. 463 - 473 (2020/07/03)
A simple method to prepare azaarenesulfonyl chlorides by NaClO2-mediated oxidative chlorination of azaarenethiols have been developed, with water as the solvent. Easy purification by simple extraction and concentration gives the products in good yields. The azaarenesulfonyl chlorides readily undergo condensation with chiral amines to afford chiral sulfonamides.
Enantioselective C-C bond formation to sulfonylimines through use of the 2-pyridinesulfonyl group as a novel stereocontroller
Nakamura, Shuichi,Nakashima, Hiroki,Sugimoto, Hideki,Sano, Hideaki,Hattori, Masataka,Shibata, Norio,Toru, Takeshi
scheme or table, p. 2145 - 2152 (2009/04/08)
Enantioselective C-C bond formation to 2-pyridinesulfonylimines afforded products with good enantioselectivity. Dynamic induction of chirality on the sulfur by coordination of a chiral Lewis acid to the pyridine nitrogen and one of the prochiral sulfonyl oxygens induces enantioselectivity. Since the 2-pyridine-sulfonyl group can easily be removed after the reaction, it acts not only as an activating group but also as an efficient Stereocontroller.
Enantioselective nucleophilic addition to N-(2-pyridylsulfonyl)imines by use of dynamically induced chirality
Sugimoto, Hideki,Nakamura, Shuichi,Hattori, Masataka,Ozeki, Sachiko,Shibata, Norio,Toru, Takeshi
, p. 8941 - 8944 (2007/10/03)
Enantioselective nucleophilic addition of Grignard reagents to N-(2-pyridylsulfonyl)imines in the presence of bis(oxazoline) afforded products with good enantioselectivity. Dynamically induced chiralitxy on the sulfur by coordination of a chiral Lewis aci
Dication C(R1)-N(R2)2 synthons and their use in the synthesis of formamidines, amidines, and α-aminonitriles
Cai, Lisheng,Han, Ying,Ren, Sumei,Huang, Liangfu
, p. 8253 - 8262 (2007/10/03)
A combination of amides and 2-pyridinesulfonyl chloride was evaluated as synthons of the dication C(R1)-N(R2)2/2+. When the substrates were primary amines, high yields of formamidines and amidines were obtained. When the substrates were α-aminoamides, α-aminonitriles were obtained. Through this process, naturally occurring α-aminoacids can be transformed into chiral α-aminonitriles with complete retention of stereochemical configuration. All reactions proceed rapidly at room temperature, and normally finish within 10 min, with yields ranging from 80 to 95% for most cases. Among the sulfonyl chlorides examined, 2-pyridinesulfonyl chloride stands out in both reaction rate and selectivity of formamidine or amidine versus sulfonyl amide. The scope and limitations of the reaction among different types of amides as synthons and amines as substrates were examined. (C) 2000 Elsevier Science Ltd.
