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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
Source PublicationORGANIC LETTERS
2011-03-04
DOI10.1021/ol102933q
Volume13Issue:5Pages:876-879
Indexed BySCI ; IC ; CCR
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordASYMMETRIC ALDOL REACTIONS ; INTERMOLECULAR ALPHA-ALKYLATION ; BOND-FORMING REACTIONS ; CONJUGATE ADDITIONS ; ENAMINE CATALYSIS ; CINCHONA ALKALOIDS ; ORGANIC CATALYSIS ; MANNICH REACTIONS ; NATURAL-PRODUCT ; DESIGN
AbstractA 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.
Language英语
WOS IDWOS:000287645800014
Citation statistics
Cited Times:33[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/142590
Collection中国科学院大连化学物理研究所
Affiliation1.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
Recommended Citation
GB/T 7714
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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