Catalytic Enantioselective Intermolecular Desymmetrization of Azetidines.
The first catalytic asymmetric desymmetrization of azetidines is disclosed. Despite the low propensity of azetidine ring opening and challenging stereocontrol, smooth intermolecular reactions were realized with excellent efficiency and enantioselectivity. These were enabled by the suitable combinati...
| Publicado en: | Journal of the American Chemical Society Vol. 137; no. 18; pp. 5895 - 5899 |
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| Autores principales: | , , , , , |
| Formato: | Artículo |
| Publicado: |
American Chemical Society
5/13/2015
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| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=102932103&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 102932103 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 5/13/2015 vid: 137 iid: 18 pid: 997 pub: American Chemical Society artinfo: ui: 102932103 10.1021/jacs.5b03083 ppf: 5895 ppct: 4 formats: tig: atl: Catalytic Enantioselective Intermolecular Desymmetrization of Azetidines. aug: au: Zhaobin Wang Fu Kit Sheong Sung, Herman H. Y. Williams, Ian D. Zhenyang Lin Jianwei Sun affil: Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China su: Enantioselective catalysis Azetidine Density functional theory Curtin-Hammett principle Amine derivatives sug: subj: Enantioselective catalysis Azetidine Density functional theory Curtin-Hammett principle Amine derivatives ab: The first catalytic asymmetric desymmetrization of azetidines is disclosed. Despite the low propensity of azetidine ring opening and challenging stereocontrol, smooth intermolecular reactions were realized with excellent efficiency and enantioselectivity. These were enabled by the suitable combination of catalyst, nucleophile, protective group, and reaction conditions. The highly enantioenriched densely functionalized products are versatile precursors to other useful chiral molecules. Mechanistic studies, including DFT calculations, revealed that only one catalyst molecule is involved in the key transition state, though both reactants can be activated. Also, the Curtin--Hammett principle dictates the reaction proceeds via amide nitrogen activation. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2015 holdings: @attributes: islocal: N |
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