Stereoselective synthesis of 2,6-disubstituted 3-piperidinols: application to the expedient synthesis of (+)-julifloridine |
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Authors: | Lemire Alexandre Charette André B |
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Affiliation: | Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec H3C 3J7, Canada. |
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Abstract: | [reaction: see text] The asymmetric synthesis of 2,6-disubstituted 3-piperidinols having a 2,3-cis and 2,6-trans relative stereochemistry was accomplished in three steps using the following sequence: stereocontrolled nucleophilic addition of an organomagnesium reagent to a chiral pyridinium salt; monohydrogenation of the resulting 2-substituted 1,2-dihydropyridine; and a one-pot, highly diastereoselective epoxidation-nucleophilic addition with a heteroatom nucleophile or an organometallic reagent. This methodology was applied to the expedient asymmetric synthesis of (+)-julifloridine in four steps. |
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