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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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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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| Subjects: | Q Science > QD Chemistry | ||||||||||||
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||||||
| Library of Congress Subject Headings (LCSH): | Chirality, Amines -- Synthesis, Amino acids, Chemistry, Organic | ||||||||||||
| Journal or Publication Title: | Tetrahedron | ||||||||||||
| Publisher: | Pergamon | ||||||||||||
| ISSN: | 0040-4020 | ||||||||||||
| Official Date: | 25 September 2019 | ||||||||||||
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| 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 | ||||||||||||
| RIOXX Funder/Project Grant: |
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