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Verona, Italy

Andreotti D.,GSK Spa | Miserazzi E.,GSK Spa | Nalin A.,GSK Spa | Pozzan A.,GSK Spa | And 2 more authors.
Tetrahedron Letters | Year: 2010

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-alkylpyridine N-oxide derivatives using (R) Mosher's acyl chloride as activator of the rearrangement to give, after hydrolysis, enantiomerically enriched 1-(2-pyridinyl)alkyl alcohol. Diastereoselectivity of the process was studied at low temperatures in different solvents, and was supported by a preliminary in silico modeling. © 2010 Elsevier Ltd. All rights reserved.

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