Simple Open-Chain Phosphite-Olefin as Ligand for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Enantioselective Access to gem-Diaryl alpha-Amino Acid Derivatives

doi:10.1021/acscatal.5b02403

	Simple Open-Chain Phosphite-Olefin as Ligand for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Enantioselective Access to gem-Diaryl alpha-Amino Acid Derivatives
	Li, Yi; Yu, Yue-Na; Xu, Ming-Hua
刊名	ACS CATALYSIS
	2016-02
卷号	6 期号:2 页码:661-665
关键词	asymmetric catalysis rhodium arylation cyclic ketimine P-olefin ligand alpha-amino acid
ISSN号	2155-5435
DOI	10.1021/acscatal.5b02403
文献子类	Article
英文摘要	A new class of open-chain chiral phosphite based hybrid olefin ligands has been developed and utilized in Rh-catalyzed asymmetric arylation of 1,2,5-thiadiazolidine 1,1-dioxide type cyclic ketimines. The reactions generate quaternary carbon-containing, gem-diaryl-substituted sulfahydantoins and 4-ethoxy-2,3-dihydro-1,2,S-thiadiazole 1,1-dioxides with excellent enantioselectivities under exceptionally mild and user-friendly conditions using a H-8-binol-derived phosphite-olefin ligand. The method is useful in offering efficient and convenient synthesis of enantioriched alpha,alpha-diaryl-alpha-amino acid amides and nitrogen-containing heterocycles. Furthermore, by taking advantage of the protocol, the first enantioselective synthesis of BACE1 inhibitor (R)-iminohydantoin has been accomplished.
资助项目	National Science Foundation of China[21325209] ; National Science Foundation of China[21472205] ; Shanghai Municipal Committee of Science and Technology (Program of Shanghai Academic Research Leader)[14XD1404400]
WOS关键词	N-SULFONYL KETIMINES ; MECHANISM-BASED INHIBITORS ; STRUCTURE-BASED DESIGN ; ARYL BORONIC ACIDS ; EFFICIENT SYNTHESIS ; ARYLBORONIC ACIDS ; NUCLEOPHILIC ALLYLATION ; BACE1 INHIBITORS ; SULFUR-OLEFINS ; CHIRAL LIGANDS
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000369774900020
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/276161]
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药物靶标结构与功能中心
通讯作者	Xu, Ming-Hua
作者单位	Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China
推荐引用方式 GB/T 7714	Li, Yi,Yu, Yue-Na,Xu, Ming-Hua. Simple Open-Chain Phosphite-Olefin as Ligand for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Enantioselective Access to gem-Diaryl alpha-Amino Acid Derivatives[J]. ACS CATALYSIS,2016,6(2):661-665.
APA	Li, Yi,Yu, Yue-Na,&Xu, Ming-Hua.(2016).Simple Open-Chain Phosphite-Olefin as Ligand for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Enantioselective Access to gem-Diaryl alpha-Amino Acid Derivatives.ACS CATALYSIS,6(2),661-665.
MLA	Li, Yi,et al."Simple Open-Chain Phosphite-Olefin as Ligand for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Enantioselective Access to gem-Diaryl alpha-Amino Acid Derivatives".ACS CATALYSIS 6.2(2016):661-665.