Chemical Dynamic Thermodynamic Resolution and S/R Interconversion of Unprotected Unnatural Tailor-made alpha-Amino Acids

doi:10.1021/acs.joc.5b01292

	Chemical Dynamic Thermodynamic Resolution and S/R Interconversion of Unprotected Unnatural Tailor-made alpha-Amino Acids
	Wang, Shuni 2; Zhou, Shengbin 2; Wang, Jiang2 ; Yong Nian 2; Kawashima, Aid 1; Moriwaki, Hiroki 1; Acena, Jose L.4; Sooshonok, Vadim A.3,4; Liu, Hong2
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2015-10-16
卷号	80 期号:20 页码:9817-9830
ISSN号	0022-3263
DOI	10.1021/acs.joc.5b01292
文献子类	Article
英文摘要	Described here is an advanced, general method for purely chemical dynamic thermodynamic resolution and S/R interconversion of unprotected tailor-made alpha-amino acids (alpha-AAs) through intermediate formation of the corresponding nickel(11)-chelated Schiff bases. The method features virtually complete stereochemical outcome, broad substrate generality (35 examples), and operationally convenient conditions allowing for large-scale preparation of the target alpha-AAs in enantiomerically pure form. Furthermore, the new type of nonracemizable axially chiral ligands can be quantitatively recycled and reused, rendering the whole process economically and synthetically attractive.
资助项目	National Natural Science Foundation of China[81302633] ; National Natural Science Foundation of China[21472209] ; National Natural Science Foundation of China[91229204] ; National High Technology Research and Development Program of China[2012AA020302] ; Chinese National Programs for Fundamental Research and Development[2015CB910304]
WOS关键词	ENANTIOSELECTIVE BIOMIMETIC TRANSAMINATION ; CONVENIENT ASYMMETRIC-SYNTHESIS ; KINETIC RESOLUTION ; (R)-3-AMINO-4,4,4-TRIFLUOROBUTANOIC ACID ; AZLACTONES ; DERIVATIVES ; EFFICIENT ; PEPTIDES ; ORGANOCATALYSTS ; HYDROGENATION
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000363224600002
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/276358]
专题	药物化学研究室
通讯作者	Sooshonok, Vadim A.
作者单位	1.Hamad Chem Ltd, Higashi Yodogawa Ku, Osaka 5330024, Japan; 2.Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, Shanghai 201203, Peoples R China; 3.Ikerbasque, Basque Fdn Sci, Bilbao 48011, Spain 4.Univ Basque Country, UPV EHU, Fac Chem, Dept Organ Chem 1, San Sebastian 20018, Spain;
推荐引用方式 GB/T 7714	Wang, Shuni,Zhou, Shengbin,Wang, Jiang,et al. Chemical Dynamic Thermodynamic Resolution and S/R Interconversion of Unprotected Unnatural Tailor-made alpha-Amino Acids[J]. JOURNAL OF ORGANIC CHEMISTRY,2015,80(20):9817-9830.
APA	Wang, Shuni.,Zhou, Shengbin.,Wang, Jiang.,Yong Nian.,Kawashima, Aid.,...&Liu, Hong.(2015).Chemical Dynamic Thermodynamic Resolution and S/R Interconversion of Unprotected Unnatural Tailor-made alpha-Amino Acids.JOURNAL OF ORGANIC CHEMISTRY,80(20),9817-9830.
MLA	Wang, Shuni,et al."Chemical Dynamic Thermodynamic Resolution and S/R Interconversion of Unprotected Unnatural Tailor-made alpha-Amino Acids".JOURNAL OF ORGANIC CHEMISTRY 80.20(2015):9817-9830.