Synthesis of gem-disubstituted taurines by the regioselective ring-opening of 2,2-disubstituted aziridines with sodium bisulfite and sulfite.
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.
Chen
Ning
N
Faculty of Science, Beijing University of Chemical Technology, 100029 Beijing, China.
Zhu
Min
M
Zhang
Wei
W
Du
Da-Ming
DM
Xu
Jiaxi
J
D001388:Aziridines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013447:Sulfites / Q000737:chemistry*; D013654:Taurine / Q000138:chemical synthesis / Q000737:chemistry
D001388:Aziridines; D013447:Sulfites; D013654:Taurine; C009279:sodium bisulfite; C025026:sodium sulfite