Molecular Assembly of an Achiral Phosphine and a Chiral Primary Amine: A Highly Efficient Supramolecular Catalyst for the Enantioselective Michael Reaction of Aldehydes with Maleimides

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	Molecular Assembly of an Achiral Phosphine and a Chiral Primary Amine: A Highly Efficient Supramolecular Catalyst for the Enantioselective Michael Reaction of Aldehydes with Maleimides
	Yang W(杨伟)1; Jiang KZ(蒋可志)1; Lu X(鲁幸)1; Yang HM(杨化萌)1; Li L(李莉)1; Lu YX(卢一新)3,4; Xu LW(徐利文)1,2
刊名	Chemistry - An Asian Journal
	2013
卷号	8 期号:6 页码:1182-1190
关键词	aldehydes Michael addition molecular assembly organocatalysis supramolecular chemistry
ISSN号	1861-4728
通讯作者	徐利文
英文摘要	A combined catalyst system of a cinchonidine-derived primary amine and triphenylphosphine (CDNH₂/PPh₃) exhibited high catalytic performance in the Michael reaction of aldehydes with maleimides, thereby affording the corresponding functionalized aldehydes in excellent yields (up to 99%) and enantioselectivities (>99% ee). More interestingly, the significance of the phosphine in enhancing the enantioselectivities in the chiral-primary-amine-catalyzed Michael reaction was revealed. Furthermore, we explored the origin of the reaction mechanism in the Michael addition promoted by the dual organocatalytic system. On the basis of experimental results and spectroscopic analysis, such as UV/Vis, fluorescence emission (FL), NMR, and circular dichroism (CD) spectroscopy, as well as ESI-MS, we found that the molecular assembly of phosphine and primary amine played a crucial role in this enantioselective reaction, in which a possible supramolecular complex was formed as an effective chiral catalyst through noncovalent molecular interactions of a cinchona alkaloid-derived primary amine with triphenylphosphine.
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, 20973051;21173064);the Zhejiang Provincial Natural Science Foundation of China (ZPNSFC, Q12B020037);the Program for Excellent Young Teachers in Hangzhou Normal University (HNUEYT, JTAS 2011-01-014)
语种	英语
WOS记录号	WOS:000319424300017
公开日期	2013-12-24
内容类型	期刊论文
源URL	[http://210.77.64.217/handle/362003/4865]
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 3.Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore 4.Natl Univ Singapore, Inst Life Sci, Med Chem Program, Singapore 117543, Singapore
推荐引用方式 GB/T 7714	Yang W,Jiang KZ,Lu X,et al. Molecular Assembly of an Achiral Phosphine and a Chiral Primary Amine: A Highly Efficient Supramolecular Catalyst for the Enantioselective Michael Reaction of Aldehydes with Maleimides[J]. Chemistry - An Asian Journal,2013,8(6):1182-1190.
APA	Yang W.,Jiang KZ.,Lu X.,Yang HM.,Li L.,...&Xu LW.(2013).Molecular Assembly of an Achiral Phosphine and a Chiral Primary Amine: A Highly Efficient Supramolecular Catalyst for the Enantioselective Michael Reaction of Aldehydes with Maleimides.Chemistry - An Asian Journal,8(6),1182-1190.
MLA	Yang W,et al."Molecular Assembly of an Achiral Phosphine and a Chiral Primary Amine: A Highly Efficient Supramolecular Catalyst for the Enantioselective Michael Reaction of Aldehydes with Maleimides".Chemistry - An Asian Journal 8.6(2013):1182-1190.