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题名: Formal Asymmetric Catalytic Thiolation witha Bifunctional Catalyst at a Water-Oil Interface: Synthesis of Benzyl Thiols
作者: Guo, Wengang1;  Wu, Bo1;  Zhou, Xin1;  Chen, Ping1;  Wang, Xu1;  Zhou, Yong-Gui1;  Liu, Yan1;  Li, Can1
关键词: asymmetric catalysis ;  organocatalysis ;  ortho-quinone methides ;  thiol addition
刊名: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
发表日期: 2015-04-07
DOI: 10.1002/anie.201409894
卷: 54, 期:15, 页:4522-4526
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Multidisciplinary
研究领域[WOS]: Chemistry
英文摘要: The enantioselective conjugated addition of tritylthiol to insitu generated ortho-quinone methides (o-QMs) is catalyzed by an acid-base bifunctional squaramide organocatalyst. The transformation proceeds with high yield (up to 99%) and stereoselectivity (up to 97:3 e.r.) using water as solvent under mild conditions. The catalyst system provides a new strategy for the synthesis of optically active benzyl mercaptans. Control experiments suggested that o-QMs are generated by the tertiary amine moiety of the squaramide organocatalyst and that the water-oil biphase is crucial for achieving high reactivity and stereoselectivity.
关键词[WOS]: O-QUINONE METHIDES ;  HYDROGEN-BOND DONORS ;  MICHAEL ADDITION ;  ENANTIOSELECTIVE ADDITION ;  CONJUGATE ADDITION ;  EMULSION DROPLETS ;  SQUARAMIDE DERIVATIVES ;  CINCHONA ALKALOIDS ;  ORGANIC CATALYST ;  DOMINO REACTIONS
语种: 英语
WOS记录号: WOS:000352497600019
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/146175
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

Recommended Citation:
Guo, Wengang,Wu, Bo,Zhou, Xin,et al. Formal Asymmetric Catalytic Thiolation witha Bifunctional Catalyst at a Water-Oil Interface: Synthesis of Benzyl Thiols[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2015,54(15):4522-4526.
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