Please use this identifier to cite or link to this item:
https://doi.org/10.1021/jacs.0c03447
Title: | Single-Step Enantioselective Synthesis of Mechanically Planar Chiral [2]Rotaxanes Using a Chiral Leaving Group Strategy | Authors: | Tian, Chong Fielden, Stephen DP Perez-Saavedra, Borja Vitorica-Yrezabal, Inigo J Leigh, David A |
Keywords: | Science & Technology Physical Sciences Chemistry, Multidisciplinary Chemistry ROTAXANES RESOLUTION CATALYSIS SEQUENCE BOND |
Issue Date: | 27-May-2020 | Publisher: | AMER CHEMICAL SOC | 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 | 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. | Source Title: | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | URI: | https://scholarbank.nus.edu.sg/handle/10635/241764 | ISSN: | 0002-7863 1520-5126 |
DOI: | 10.1021/jacs.0c03447 |
Appears in Collections: | Staff Publications Elements |
Show full item record
Files in This Item:
File | Description | Size | Format | Access Settings | Version | |
---|---|---|---|---|---|---|
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 |
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.