Organic Letters 2004-10-28

Notable coordination effects of 2-pyridinesulfonamides leading to efficient aziridination and selective aziridine ring opening.

Hoon Han, Imhyuck Bae, Eun Jeong Yoo, Junseong Lee, Youngkyu Do, Sukbok Chang

Index: Org. Lett. 6(22) , 4109-12, (2004)

Full Text: HTML

Abstract

[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.