Chiral ligand 2-(2′-piperidinyl)pyridine:: synthesis, resolution and application in asymmetric diethylzinc addition to aldehydes

Chiral ligand 2-(2'-piperidinyl)pyridine 1 has been synthesized in good overall yield by sequential benzylation, hydrogenation and debenzylation of 2,2'-bipyridine. Its enantiomerically pure enantiomers have been obtained by resolution of 2-(1-benzyl-2-piperidinyl)pyridine 2 with D-tartaric acid (or L-tartaric acid) followed by debenzylation. The absolute configuration was determined by X-ray analysis of the (S)-2 D-tartrate. It was demonstrated that I can be used as an effective enantioselective catalyst in the addition of diethylzinc to aldehydes. Optically active secondary alcohols with up to 100% enantiomeric excess were obtained in high yields. (C) 2008 Elsevier Ltd. All rights reserved.