Chiral organomagnesiates as dual reagents for bromine-magnesium exchange of 2-bromopyridine and access to chiral α-substituted 2-pyridylcarbinols - Université de Rennes Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2012

Chiral organomagnesiates as dual reagents for bromine-magnesium exchange of 2-bromopyridine and access to chiral α-substituted 2-pyridylcarbinols

Résumé

New chiral ligand containing butyl and dibutylmagnesiates have been prepared from a range of ligands and their reactivity studied. The reagents were generally efficient in promoting the clean bromine-magnesium exchange of 2-bromopyridine at room temperature and the subsequent reaction with aldehydes to afford α-substituted 2-pyridylcarbinols in good yields. (R,R)-TADDOLate proved to be the best ligand, leading to acceptable to good enantioselectivities. To the best of our knowledge this is the first example of an organomagnesiate-induced halogen-metal exchange followed by an enantioselective addition.

Domaines

Chimie organique

Dates et versions

hal-01053767 , version 1 (01-08-2014)

Identifiants

Citer

Delphine Catel, Floris Chevallier, Florence Mongin, Philippe C. Gros. Chiral organomagnesiates as dual reagents for bromine-magnesium exchange of 2-bromopyridine and access to chiral α-substituted 2-pyridylcarbinols. European Journal of Organic Chemistry, 2012, pp.53-57. ⟨10.1002/ejoc.201101490⟩. ⟨hal-01053767⟩
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