New silver(I)-monophosphine complex derived from chiral Ar-BINMOL: synthesis and catalytic activity in asymmetric vinylogous Mannich reaction

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	New silver(I)-monophosphine complex derived from chiral Ar-BINMOL: synthesis and catalytic activity in asymmetric vinylogous Mannich reaction
	Zheng LS(郑龙生)1; Li L(李莉)1; Yang KF(杨科芳)1; Zheng ZJ(郑战江)1; Xiao XQ(效旭琼)1; Xu LW(徐利文)1,2
刊名	Tetrahedron
	2013
卷号	69 期号:41 页码:8777-8784
关键词	Silver Ar-BINMOL Phosphine Vinylogous Mannich reaction Asymmetric catalysis
ISSN号	0040-4020
通讯作者	徐利文
英文摘要	A new family of C₂-axially chiral monophosphines (Ar-NNPs) from Ar-BINMOLs was developed for silvercatalyzed asymmetric vinylogous Mannich reaction of (furan-2-yloxy)trimethylsilane with aromatic aldimines. It was found that the enantioselective vinylogous Mannich-type reactions of trimethylsiloxyfuran with aldimines are catalyzed efficiently by silver(I) complexes of the Ar-BINMOL-derived chiral monophosphine. This procedure displays wide aldimine versatility, excellent yields (up to 99% isolated yields), moderate to good enantioselectivity (up to 78%ee) and exceptional diastereoselectivity (>99:1 dr) in most cases examined. The molecular structure of silveremonophosphine complex was confirmed by X-ray analysis and revealed that the benzyl group on chiral monophosphine provided dual function with weak silver-π/π-π stacking and steric repulsion to favour the diastereoselective Re-nucleophilic addition of siloxyfuran to imine.
学科主题	物理化学与绿色催化
收录类别	SCI
资助信息	the National Natural Science Foundation of China (NSFC, Nos. 21173064;51203037);Program for Excellent Young Teachers in Hangzhou Normal University (HNUEYT, JTAS 2011-01-014);Zhejiang Provincial Natural Science Foundation of China (Q12B020037)
语种	英语
WOS记录号	WOS:000324362300013
公开日期	2013-12-24
内容类型	期刊论文
源URL	[http://210.77.64.217/handle/362003/4871]
专题	兰州化学物理研究所_OSSO国家重点实验室
作者单位	1.Hangzhou Normal Univ, Minist Educ, Key Lab Organosilicon Chem & Mat Technol, Hangzhou 310012, Zhejiang, Peoples R China 2.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
推荐引用方式 GB/T 7714	Zheng LS,Li L,Yang KF,et al. New silver(I)-monophosphine complex derived from chiral Ar-BINMOL: synthesis and catalytic activity in asymmetric vinylogous Mannich reaction[J]. Tetrahedron,2013,69(41):8777-8784.
APA	Zheng LS,Li L,Yang KF,Zheng ZJ,Xiao XQ,&Xu LW.(2013).New silver(I)-monophosphine complex derived from chiral Ar-BINMOL: synthesis and catalytic activity in asymmetric vinylogous Mannich reaction.Tetrahedron,69(41),8777-8784.
MLA	Zheng LS,et al."New silver(I)-monophosphine complex derived from chiral Ar-BINMOL: synthesis and catalytic activity in asymmetric vinylogous Mannich reaction".Tetrahedron 69.41(2013):8777-8784.