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	Copper(ii)-mediated resolution of alpha-halo carboxylic acids with chiral o,o '-dibenzoyltartaric acid: spontaneous racemization and crystallization-induced dynamic resolution
	Xu, HW; Wang, QW; Zhu, J; Deng, JG; Cun, LF; Cui, X; Wu, J; Xu, XL; Wu, YL
刊名	Organic & biomolecular chemistry
	2005
卷号	3期号:23页码:4227-4232
ISSN号	1477-0520
DOI	10.1039/b510170k
通讯作者	Deng, jg()
英文摘要	Herein we present a new example of coordination-mediated resolution of racemic acids by a chiral acid. the reaction of copper(ii) acetate monohydrate, optically pure o,o'-dibenzoyltartaric acid ( dbta) and racemic alpha-bromo-2-chlorophenylacetic acid (hl1) in acetonitrile solution afforded a binuclear copper(ii) complex with d-dbta dianion, alpha-bromo-2-chlorophenylacetate and acetate as ligands. after decomposition of the complex with acid, the optically active acid ((r)-hl1) was obtained. similarly, alpha-bromo-2-fluorophenylacetic acid (hl2), alpha-bromo-2-bromophenylacetic acid (hl3), alpha-chloro-2-chlorophenylacetic acid (hl4), alpha-chloro-2-fluorophenylacetic acid (hl5), alpha-bromophenylacetic acid (hl6), alpha-bromo-4-chlorophenylacetic acid (hl7), 2-bromopropionic acid (hl8) and 2-chloropropionic acid (hl9) were resolved by the same method. satisfactory results were obtained for hl2 to hl5. for hl6 and hl7, only racemic acids were obtained. for the two alpha-halo aliphatic acids (hl8 and hl9), poor enantioselectivity was obtained. it is more interesting that three acids (hl1, hl2 and hl3) could spontaneously racemize in acetonitrile solution, which resulted in crystallization-induced dynamic resolution (cidr) with greater than 50% yield.
WOS关键词	ASYMMETRIC TRANSFORMATION ; ANTIINFLAMMATORY DRUGS ; OPTICAL RESOLUTION ; AMINO-ACIDS ; COMPLEXES ; COORDINATION ; RECOGNITION ; LIGANDS
WOS研究方向	Chemistry
WOS类目	Chemistry, Organic
语种	英语
出版者	ROYAL SOC CHEMISTRY
WOS记录号	WOS:000233362000008
内容类型	期刊论文
URI标识	http://www.corc.org.cn/handle/1471x/2377314
专题	中国科学院大学
通讯作者	Deng, JG
作者单位	1.Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu 610041, Peoples R China 2.Chinese Acad Sci, Chengdu Inst Organ Chem, Union Lab Asymmetr Synth, Chengdu 610041, Peoples R China 3.Zhejiang APELOA Med Technol Co Ltd, Dongyang 322118, Peoples R China 4.Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
推荐引用方式 GB/T 7714	Xu, HW,Wang, QW,Zhu, J,et al. Copper(ii)-mediated resolution of alpha-halo carboxylic acids with chiral o,o '-dibenzoyltartaric acid: spontaneous racemization and crystallization-induced dynamic resolution[J]. Organic & biomolecular chemistry,2005,3(23):4227-4232.
APA	Xu, HW.,Wang, QW.,Zhu, J.,Deng, JG.,Cun, LF.,...&Wu, YL.(2005).Copper(ii)-mediated resolution of alpha-halo carboxylic acids with chiral o,o '-dibenzoyltartaric acid: spontaneous racemization and crystallization-induced dynamic resolution.Organic & biomolecular chemistry,3(23),4227-4232.
MLA	Xu, HW,et al."Copper(ii)-mediated resolution of alpha-halo carboxylic acids with chiral o,o '-dibenzoyltartaric acid: spontaneous racemization and crystallization-induced dynamic resolution".Organic & biomolecular chemistry 3.23(2005):4227-4232.

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