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

被引：20
|
作者：
Cheng, Yan-Qin [1 ]
Bian, Zheng [1 ]
Kang, Chuan-Qing [1 ]
Guo, Hai-Quan [1 ]
Gao, Lian-Xun [1 ]
机构：
[1] Chinese Acad Sci, Changchun Inst Appl Chem, Grad Sch, State Key Lab Polymer Phys & Chem, Changchun 130022, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 13期
关键词：
D O I：
10.1016/j.tetasy.2008.06.005
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
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.
引用
收藏
页码：1572 / 1575
页数：4
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