Tetrahedron: Asymmetry

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

YQ Cheng, Z Bian, CQ Kang, HQ Guo, LX Gao

Index: Cheng, Yan-Qin; Bian, Zheng; Kang, Chuan-Qing; Guo, Hai-Quan; Gao, Lian-Xun Tetrahedron Asymmetry, 2008 , vol. 19, # 13 p. 1572 - 1575

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Citation Number: 22

Abstract

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)-2d-tartrate. It was ...