Pentanidium-Catalyzed Direct Assembly of Vicinal All-Carbon Quaternary Stereocenters through C(sp^(3))–C(sp^(3))Bond Formation  

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作  者:Xu Ban Yifan Fan Tuan-Khoa Kha Richmond Lee Choon Wee Kee Zhiyong Jiang Choon-Hong Tan 

机构地区:[1]International Scientific and Technological Cooperation Base of Chiral Chemistry,Henan University,Kaifeng 475004 [2]Division of Chemistry and Biological Chemistry,Nanyang Technological University,Singapore 637371 [3]School of Chemistry and Molecular Bioscience,University of Wollongong,Wollongong,NSW 2522 [4]Molecular Horizons,University of Wollongong,Wollongong,NSW 2522 [5]Process&Catalysis Research,Institute of Chemical and Engineering Sciences,Singapore 627899

出  处:《CCS Chemistry》2021年第10期2192-2200,共9页中国化学会会刊(英文)

基  金:support from Nanyang Technological University for Tier 1 grants(RG1/19 and RG2/20)and Ministry of Education(Singapore)Tier 2 grants(no.MOE2019-T2-1-091);the University of Wollongong(VC Fellowship)and the Australian Research Council(DECRA DE210100053).

摘  要:The stereoselective construction of vicinal all-carbon quaternary stereocenters has long been a formidable synthetic challenge.Direct asymmetric coupling of a tertiary carbon nucleophile with a tertiary carbon electrophile is themost straightforward approach,but it is sterically and energetically disfavored.Herein,we describe a catalytic asymmetric substitution,where racemic tertiary bromides coupled directly with racemic secondary or tertiary carbanion.

关 键 词:ion-paired catalyst asy mmetric substitu-tion SN2 substitution SN2X substitution all-carbon quaternary stere ocenters 

分 类 号:O62[理学—有机化学]

 

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