Stable aziridinium salts as versatile intermediates: isolation and regio- and stereoselective ring-opening and rearrangement.
Rock trapping and exploration: Aziridinium bromide salts were discovered serendipitously during bromination of N,N-dicarboxymethylated beta-amino alcohols. Regiospecific ring-opening and rearrangement of the isolated, surprisingly stable aziridinium salts produces useful molecules including C-functionalized oxomorpholines and alpha,beta-unsaturated amines.
Song
Hyun A
HA
Chemistry Division, Biological, Chemical, and Physical Sciences Department, Illinois Institute of Technology, Chicago, IL, USA.
Dadwal
Mamta
M
Lee
Yeseul
Y
Mick
Emily
E
Chong
Hyun-Soon
HS
D000588:Amines / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D002412:Cations / Q000138:chemical synthesis / Q000737:chemistry; D054879:Halogenation; D009025:Morpholines / Q000737:chemistry; D012492:Salts / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D000605:Amino Alcohols; D001388:Aziridines; D002412:Cations; D009025:Morpholines; D012492:Salts