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(S)-(−)-Fluorenylethylchloroformate (FLEC) ; preparation using asymmetric transfer hydrogenation and application to the analysis and resolution of amines
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Amin, Mohammad A., Camerino, Michelle A., Mountford, Simon J., Ma, Xiao, Manallack, David T., Chalmers, David K., Wills, Martin and Thompson, Philip E. (2019) (S)-(−)-Fluorenylethylchloroformate (FLEC) ; preparation using asymmetric transfer hydrogenation and application to the analysis and resolution of amines. Tetrahedron, 75 (43). 130591. doi:10.1016/j.tet.2019.130591
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WRAP-Fluorenylethylchloroformate-preparation-asymmetric-hydrogenation-Wills-2019.pdf - Accepted Version Embargoed item. Restricted access to Repository staff only until 9 September 2020. Contact author directly, specifying your specific needs. - Requires a PDF viewer. Available under License Creative Commons Attribution Non-commercial No Derivatives 4.0. Download (728Kb) |
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WRAP-supporting-information-Wills-2019.pdf - Supplemental Material Embargoed item. Restricted access to Repository staff only until 9 September 2020. Contact author directly, specifying your specific needs. - Requires a PDF viewer. Available under License Creative Commons Attribution Non-commercial No Derivatives 4.0. Download (4Mb) |
Official URL: http://dx.doi.org/10.1016/j.tet.2019.130591
Abstract
Fluorenylethylchoroformate (FLEC) is a valuable chiral derivatisation reagent that is used for the resolution of a wide variety of chiral amines. Herein, we describe an improved preparation of (S)-(−)-FLEC using an efficient asymmetric catalytic transfer hydrogenation as the key step. We also demonstrate the application of FLEC as a chiral Fmoc equivalent for chiral resolution, with facile deprotection, of tetrahydroquinaldines, and its capacity for inducing regioselective outcomes in nitration reactions.
| Item Type: | Journal Article | ||||||||
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| Divisions: | Faculty of Science > Chemistry | ||||||||
| Journal or Publication Title: | Tetrahedron | ||||||||
| Publisher: | Pergamon | ||||||||
| ISSN: | 0040-4020 | ||||||||
| Official Date: | 25 September 2019 | ||||||||
| Dates: |
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| Date of first compliant deposit: | 13 September 2019 | ||||||||
| Volume: | 75 | ||||||||
| Number: | 43 | ||||||||
| Article Number: | 130591 | ||||||||
| DOI: | 10.1016/j.tet.2019.130591 | ||||||||
| Status: | Peer Reviewed | ||||||||
| Publication Status: | Published | ||||||||
| Access rights to Published version: | Restricted or Subscription Access |
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