Nucleophile-dependent regioselective ring opening of 2-substituted N,N-dibenzylaziridinium ions: bromide versus hydride.
The ring opening of 2-substituted N,N-dibenzylaziridinium ions by bromide exclusively occurs at the substituted aziridine carbon atom in a stereospecific way, whereas the opposite regioselectivity was observed for hydride-induced ring opening at the unsubstituted position; furthermore, this unprecedented hydride-promoted reactivity was validated by means of Density Functional Theory (DFT) calculations.
Yun
Sae Young
SY
Department of Chemistry, Sogang University, Seoul, Korea.
Catak
Saron
S
Lee
Won Koo
WK
D'hooghe
Matthias
M
De Kimpe
Norbert
N
Van Speybroeck
Veronique
V
Waroquier
Michel
M
Kim
Yongeun
Y
Ha
Hyun-Joon
HJ
D001388:Aziridines / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D013379:Substrate Specificity; D013816:Thermodynamics
D001388:Aziridines; D001965:Bromides