Reaction of 2-alkyl pyridine N-oxide derivatives with Mosher’s acyl chloride: first example of stereoselective Boekelheide rearrangement
✍ Scribed by Daniele Andreotti; Emanuele Miserazzi; Arnaldo Nalin; Alfonso Pozzan; Roberto Profeta; Simone Spada
- Book ID
- 104098432
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- French
- Weight
- 389 KB
- Volume
- 51
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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.