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

doi:10.1016/j.tetasy.2008.06.005

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	Chiral ligand 2-(2 '-piperidinyl)pyridine: synthesis, resolution and application in asymmetric diethylzinc addition to aldehydes
	Cheng, Yan-Qin; Bian, Zheng; Kang, Chuan-Qing; Guo, Hai-Quan; Gao, Lian-Xun
刊名	TETRAHEDRON-ASYMMETRY
	2008-07-11
卷号	19 期号:13 页码:1572-1575
ISSN号	0957-4166
DOI	10.1016/j.tetasy.2008.06.005
英文摘要	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.
语种	英语
出版者	PERGAMON-ELSEVIER SCIENCE LTD
WOS记录号	WOS:000258433400009
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/64225]
专题	中国科学院化学研究所
通讯作者	Gao, Lian-Xun
作者单位	Chinese Acad Sci, Changchun Inst Appl Chem, Grad Sch, State Key Lab Polymer Phys & Chem, Changchun 130022, Peoples R China
推荐引用方式 GB/T 7714	Cheng, Yan-Qin,Bian, Zheng,Kang, Chuan-Qing,et al. Chiral ligand 2-(2 '-piperidinyl)pyridine: synthesis, resolution and application in asymmetric diethylzinc addition to aldehydes[J]. TETRAHEDRON-ASYMMETRY,2008,19(13):1572-1575.
APA	Cheng, Yan-Qin,Bian, Zheng,Kang, Chuan-Qing,Guo, Hai-Quan,&Gao, Lian-Xun.(2008).Chiral ligand 2-(2 '-piperidinyl)pyridine: synthesis, resolution and application in asymmetric diethylzinc addition to aldehydes.TETRAHEDRON-ASYMMETRY,19(13),1572-1575.
MLA	Cheng, Yan-Qin,et al."Chiral ligand 2-(2 '-piperidinyl)pyridine: synthesis, resolution and application in asymmetric diethylzinc addition to aldehydes".TETRAHEDRON-ASYMMETRY 19.13(2008):1572-1575.