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A New Class of Structurally Rigid Tricyclic Chiral Secondary Amine Organocatalyst: Highly Enantioselective Organocatalytic Michael Addition of Aldehydes to Vinyl Sulfones
Xiao, Jian1,2; Lu, Yun-Peng1; Liu, Yan-Ling1; Wong, Poh-Shen1; Loh, Teck-Peng1
刊名ORGANIC LETTERS
2011-03-04
DOI10.1021/ol102933q
13期:5页:876-879
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology ; Physical Sciences
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]ASYMMETRIC ALDOL REACTIONS ; INTERMOLECULAR ALPHA-ALKYLATION ; BOND-FORMING REACTIONS ; CONJUGATE ADDITIONS ; ENAMINE CATALYSIS ; CINCHONA ALKALOIDS ; ORGANIC CATALYSIS ; MANNICH REACTIONS ; NATURAL-PRODUCT ; DESIGN
英文摘要A new class of chiral secondary amine organocatalyst was rationally designed as an efficient catalyst to catalyze the elusive Michael addition of aldehydes to vinyl sulfones. High yield and excellent enantioselectivities could be obtained at room temperature without having to resort to high catalyst loading, anhydrous solvents, and low temperatures. Efficient control of enamine conformation and face shielding as well as the rigid nature of the tricyclic skeleton, with an inherent chiral pocket, provide a well-organized chiral environment to effect this elusive reaction efficiently.
语种英语
WOS记录号WOS:000287645800014
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文献类型期刊论文
条目标识符http://cas-ir.dicp.ac.cn/handle/321008/142590
专题中国科学院大连化学物理研究所
作者单位1.Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
2.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
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Xiao, Jian,Lu, Yun-Peng,Liu, Yan-Ling,et al. A New Class of Structurally Rigid Tricyclic Chiral Secondary Amine Organocatalyst: Highly Enantioselective Organocatalytic Michael Addition of Aldehydes to Vinyl Sulfones[J]. ORGANIC LETTERS,2011,13(5):876-879.
APA Xiao, Jian,Lu, Yun-Peng,Liu, Yan-Ling,Wong, Poh-Shen,&Loh, Teck-Peng.(2011).A New Class of Structurally Rigid Tricyclic Chiral Secondary Amine Organocatalyst: Highly Enantioselective Organocatalytic Michael Addition of Aldehydes to Vinyl Sulfones.ORGANIC LETTERS,13(5),876-879.
MLA Xiao, Jian,et al."A New Class of Structurally Rigid Tricyclic Chiral Secondary Amine Organocatalyst: Highly Enantioselective Organocatalytic Michael Addition of Aldehydes to Vinyl Sulfones".ORGANIC LETTERS 13.5(2011):876-879.
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