Please use this identifier to cite or link to this item:
https://doi.org/10.1021/jacs.0c03447
DC Field | Value | |
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dc.title | Single-Step Enantioselective Synthesis of Mechanically Planar Chiral [2]Rotaxanes Using a Chiral Leaving Group Strategy | |
dc.contributor.author | Tian, Chong | |
dc.contributor.author | Fielden, Stephen DP | |
dc.contributor.author | Perez-Saavedra, Borja | |
dc.contributor.author | Vitorica-Yrezabal, Inigo J | |
dc.contributor.author | Leigh, David A | |
dc.date.accessioned | 2023-06-08T12:26:37Z | |
dc.date.available | 2023-06-08T12:26:37Z | |
dc.date.issued | 2020-05-27 | |
dc.identifier.citation | Tian, Chong, Fielden, Stephen DP, Perez-Saavedra, Borja, Vitorica-Yrezabal, Inigo J, Leigh, David A (2020-05-27). Single-Step Enantioselective Synthesis of Mechanically Planar Chiral [2]Rotaxanes Using a Chiral Leaving Group Strategy. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 142 (21) : 9803-9808. ScholarBank@NUS Repository. https://doi.org/10.1021/jacs.0c03447 | |
dc.identifier.issn | 0002-7863 | |
dc.identifier.issn | 1520-5126 | |
dc.identifier.uri | https://scholarbank.nus.edu.sg/handle/10635/241764 | |
dc.description.abstract | We report a one-step enantioselective synthesis of mechanically planar chiral [2]rotaxanes. Previous studies of such molecules have generally involved the separation of enantiomers from racemic mixtures or the preparation and separation of diastereomeric intermediates followed by post-assembly modification to remove other sources of chirality. Here, we demonstrate a simple asymmetric metal-free active template rotaxane synthesis using a primary amine, an activated ester with a chiral leaving group, and an achiral crown ether lacking rotational symmetry. Mechanically planar chiral rotaxanes are obtained directly in up to 50% enantiomeric excess. The rotaxanes were characterized by NMR spectroscopy, high-resolution mass spectrometry, chiral HPLC, single crystal X-ray diffraction, and circular dichroism. Either rotaxane enantiomer could be prepared selectively by incorporating pseudoenantiomeric cinchona alkaloids into the chiral leaving group. | |
dc.language.iso | en | |
dc.publisher | AMER CHEMICAL SOC | |
dc.source | Elements | |
dc.subject | Science & Technology | |
dc.subject | Physical Sciences | |
dc.subject | Chemistry, Multidisciplinary | |
dc.subject | Chemistry | |
dc.subject | ROTAXANES | |
dc.subject | RESOLUTION | |
dc.subject | CATALYSIS | |
dc.subject | SEQUENCE | |
dc.subject | BOND | |
dc.type | Article | |
dc.date.updated | 2023-06-06T01:41:10Z | |
dc.contributor.department | PHARMACY | |
dc.description.doi | 10.1021/jacs.0c03447 | |
dc.description.sourcetitle | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | |
dc.description.volume | 142 | |
dc.description.issue | 21 | |
dc.description.page | 9803-9808 | |
dc.published.state | Published | |
Appears in Collections: | Staff Publications Elements |
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File | Description | Size | Format | Access Settings | Version | |
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Single-Step Enantioselective Synthesis of Mechanically Planar Chiral [2]Rotaxanes Using a Chiral Leaving Group Strategy.pdf | 2.96 MB | Adobe PDF | OPEN | None | View/Download |
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