Reaction of 2-alkyl pyridine N-oxide derivatives with Mosher’s acyl chloride: first example of stereoselective Boekelheide rearrangement |
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Authors: | Daniele Andreotti |
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Institution: | Neurosciences CEDD Medicine Research Centre, GSK Spa, Via Fleming 4, 37135 Verona, Italy |
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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 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. |
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Keywords: | Boekelheide rearrangement Stereoselection 1-(2-Pyridinyl)-alkyl alcohol Mosher&rsquo s acyl chloride |
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