Reaction of 2-alkyl pyridine N-oxide derivatives with Mosher's acyl chloride: first example of stereoselective Boekelheide rearrangement

D Andreotti, E Miserazzi, A Nalin, A Pozzan, R Profeta…

Index: Andreotti, Daniele; Miserazzi, Emanuele; Nalin, Arnaldo; Pozzan, Alfonso; Profeta, Roberto; Spada, Simone Tetrahedron Letters, 2010 , vol. 51, # 50 p. 6526 - 6530

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Citation Number: 6

Abstract

Treatment of 2-alkyl pyridine N-oxides with acylating reagents represents an established procedure for the introduction of oxygen functionality into alkyl group at the ortho position of N heteroaromatic rings. We have reported the first example of asymmetric Boekelheide rearrangement applied to a set of 2-alkyl-pyridine N-oxide derivatives using (R) Mosher's acyl chloride as activator of the rearrangement to give, after hydrolysis, enantiomerically ...