Synthesis of gem-disubstituted taurines by the regioselective   ring-opening of 2,2-disubstituted aziridines with sodium bisulfite and   sulfite

doi:10.1007/s00726-008-0153-3

CORC > 北京大学 > 化学与分子工程学院

	Synthesis of gem-disubstituted taurines by the regioselective ring-opening of 2,2-disubstituted aziridines with sodium bisulfite and sulfite
	Chen, Ning ; Zhu, Min ; Zhang, Wei ; Du, Da-Ming ; Xu, Jiaxi
刊名	氨基酸
	2009
关键词	Amino acid Aminoalkanesulfonic acid Ring-opening reaction Sodium bisulfite Sodium sulfute Synthesis Taurine BETA-AMINO ACIDS SUBSTITUTED TAURINES ALCOHOLS ROUTE
DOI	10.1007/s00726-008-0153-3
英文摘要	The regioselectivity of the ring-opening reactions of 2,2-disubstituted aziridines with sodium bisulfite and sulfite showed significant divergence depending on the nucleophiles and the structure of the substituents of the aziridines. 2,2-Dialkylaziridines were specifically attacked on their less substituted carbon atoms with sodium bisulfite, affording 2,2-substituted taurines, while 2,2-disubstituted aziridines with either one or two aryl substituent(s) were attacked specifically on their more substituted carbon atoms with the same nucleophile, giving rise to aromatic 1,1-substituted taurines. Sodium sulfite attacked the less substituted carbon atoms of all aziridines specifically to afford 2,2-disubstituted taurines. The regioselectivity is governed by the nucleophile and the balance between the steric hindrance and the electronic effect. The current method provides an alternative route to the synthesis of 2,2-dialkyltaurines and aromatic gem-disubstituted taurines.; Biochemistry & Molecular Biology; SCI(E); 15; ARTICLE; 2; 309-313; 37
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/247001]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Chen, Ning,Zhu, Min,Zhang, Wei,et al. Synthesis of gem-disubstituted taurines by the regioselective ring-opening of 2,2-disubstituted aziridines with sodium bisulfite and sulfite[J]. 氨基酸,2009.
APA	Chen, Ning,Zhu, Min,Zhang, Wei,Du, Da-Ming,&Xu, Jiaxi.(2009).Synthesis of gem-disubstituted taurines by the regioselective ring-opening of 2,2-disubstituted aziridines with sodium bisulfite and sulfite.氨基酸.
MLA	Chen, Ning,et al."Synthesis of gem-disubstituted taurines by the regioselective ring-opening of 2,2-disubstituted aziridines with sodium bisulfite and sulfite".氨基酸 (2009).