Preparation of chiral enantiopure 2-(hydroxyalkyl)pyridine derivatives. Use of the chiral pool

Abstract

Enantiomerically pure 2-(1-hydroxyalkyl)pyridines were prepared via reaction of 2-lithiopyridine with (R)-2,3-O-isopropylideneglyceraldehyde, methyl (S)-2-methoxypropionate and methyl (S)-2-methoxy-2-phenylacetate, obtained from D-mannitol, L-lactic acid and L-mandelic acid, respectively. 6,6′-Bis(1-hydroxyalkyl)-2,2′-bipyridines were obtained from the same naturally occurring chiral compounds and 2-bromo-6-lithiopyridine with subsequent Ni-catalysed coupling.