BF3 x OEt2-mediated highly regioselective S(N)2-type ring-opening of N-activated aziridines and N-activated azetidines by tetraalkylammonium halides.
A highly regioselective Lewis acid-mediated S(N)2-type ring-opening of N-sulfonylaziridines and azetidines with tetraalkylammonium halides in CH(2)Cl(2) solution to afford 1,2- and 1,3-haloamines in excellent yields is described. An easy diastereoselective route toward substituted chiral N-tosylaziridines has been developed. The mechanism of ring-opening via S(N)2 pathway has been confirmed by the formation of chiral haloamines with excellent er and dr. Chloroamines obtained from 2,3-disubstituted aziridines were converted to the chiral N-tosylamines via radical dehalogenation.
Ghorai
Manas K
MK
Department of Chemistry, Indian Institute of Technology, Kanpur, 208016, India. mkghorai@iitk.ac.in
Kumar
Amit
A
Tiwari
Deo Prakash
DP
D001384:Azetidines / Q000138:chemical synthesis / Q000737:chemistry*; D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D005019:Ethyl Ethers / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D001384:Azetidines; D001388:Aziridines; D001881:Borates; D005019:Ethyl Ethers; D006846:Hydrocarbons, Halogenated; D000644:Quaternary Ammonium Compounds