Synthesis of bis-alpha,alpha '-amino acids through diastereoselective bis-alkylations of chiral Ni(II)-complexes of glycine

doi:10.1039/c3ob40594j

	Synthesis of bis-alpha,alpha '-amino acids through diastereoselective bis-alkylations of chiral Ni(II)-complexes of glycine
	Wang, Jiang1 ; Liu, Hong1 ; Luis Acena, Jose 2; Houck, Daniel 2,3; Takeda, Ryosuke 4; Moriwaki, Hiroki 4; Sato, Tatsunori 4; Soloshonok, Vadim A.2,3
刊名	ORGANIC & BIOMOLECULAR CHEMISTRY
	2013-07-21
卷号	11 期号:27 页码:4508-4515
ISSN号	1477-0520
DOI	10.1039/c3ob40594j
文献子类	Article
英文摘要	The Ni(II) complex derived from glycine Schiff base with (S)-N-(benzylprolyl)-2-aminobenzophenone can be effectively alkylated with alpha,omega-dibromide reagents to furnish the corresponding bis-alkylated products. This method presents a direct approach for the preparation of the corresponding bis-alpha,alpha'-amino acids with high biological importance. Heterogeneous (phase-transfer) as well as homogeneous conditions for the alkylation reactions have been investigated and the latter proved to be more efficient in terms of stereochemical outcome. In particular, alkylation of the glycine Schiff base Ni(II) complex with 1,3-dibromopropane followed by acid-catalysed hydrolysis of the resulting bis-alkylation product, allowed for the preparation of naturally occurring (2S,6S)-diaminopimelic acid in high overall yield.
资助项目	Ikerbasque[00000000] ; Basque Foundation for Science[00000000] ; National Natural Science Foundation of China[81025017] ; Basque Government[SAIOTEK S-PE12UN044] ; Hamari Chemicals (Osaka, Japan)[00000000]
WOS关键词	ALPHA-AMINO-ACIDS ; MICHAEL ADDITION-REACTIONS ; ASYMMETRIC ALDOL REACTIONS ; PHASE-TRANSFER CATALYSIS ; NICKEL(II) SCHIFF-BASE ; PROTECTED MESO-2,6-DIAMINOPIMELIC ACID ; OPERATIONALLY CONVENIENT CONDITIONS ; SUBSTITUTED PYROGLUTAMIC ACIDS ; PURE 4-AMINOGLUTAMIC ACIDS ; VIRTUALLY COMPLETE CONTROL
WOS研究方向	Chemistry
语种	英语
出版者	ROYAL SOC CHEMISTRY
WOS记录号	WOS:000321601000012
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/277536]
专题	药物化学研究室中科院受体结构与功能重点实验室新药研究国家重点实验室
通讯作者	Liu, Hong
作者单位	1.Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China; 2.Univ Basque Country UPV EHU, Fac Chem, Dept Organ Chem 1, San Sebastian 20018, Spain; 3.Basque Fdn Sci, IKERBASQUE, Bilbao 48011, Spain; 4.Hamari Chem Ltd, Higashi Yodogawa Ku, Osaka 5330024, Japan
推荐引用方式 GB/T 7714	Wang, Jiang,Liu, Hong,Luis Acena, Jose,et al. Synthesis of bis-alpha,alpha '-amino acids through diastereoselective bis-alkylations of chiral Ni(II)-complexes of glycine[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2013,11(27):4508-4515.
APA	Wang, Jiang.,Liu, Hong.,Luis Acena, Jose.,Houck, Daniel.,Takeda, Ryosuke.,...&Soloshonok, Vadim A..(2013).Synthesis of bis-alpha,alpha '-amino acids through diastereoselective bis-alkylations of chiral Ni(II)-complexes of glycine.ORGANIC & BIOMOLECULAR CHEMISTRY,11(27),4508-4515.
MLA	Wang, Jiang,et al."Synthesis of bis-alpha,alpha '-amino acids through diastereoselective bis-alkylations of chiral Ni(II)-complexes of glycine".ORGANIC & BIOMOLECULAR CHEMISTRY 11.27(2013):4508-4515.