Notable coordination effects of 2-pyridinesulfonamides leading to efficient aziridination and selective aziridine ring opening.
[reaction: see text] We have developed, on the basis of a chelation-strategy, an efficient copper-catalyzed aziridination protocol with the use of 5-methyl-2-pyridinesulfonamide and PhI(OAc)(2). The reaction proceeds smoothly under mild conditions to give aziridines in moderate to good yields in the absence of external ligands or bases. The coordination-assisted approach offers the additional benefits that efficient deprotection of the N-substituent and selective aziridine ring-opening are effectively achieved.
Han
Hoon
H
Center for Molecular Design and Synthesis, Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology (KAIST), Daejon 305-701, Republic of Korea.
Bae
Imhyuck
I
Yoo
Eun Jeong
EJ
Lee
Junseong
J
Do
Youngkyu
Y
Chang
Sukbok
S