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Chiral Organomagnesiates as Dual Reagents for Bromine–Magnesium Exchange of 2‐Bromopyridine and Access to Chiral α‐Substituted 2‐Pyridylcarbinols
Author(s) -
Catel Delphine,
Chevallier Floris,
Mongin Florence,
Gros Philippe C.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101490
Subject(s) - reagent , bromine , chemistry , halogen , ligand (biochemistry) , magnesium , reactivity (psychology) , enantioselective synthesis , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , medicine , biochemistry , alkyl , receptor , alternative medicine , pathology
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.