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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

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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
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
Dates:
DateEvent
25 September 2019Published
9 September 2019Available
2 September 2019Accepted
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:
Project/Grant IDRIOXX Funder NameFunder ID
UNSPECIFIEDCybek FoundationUNSPECIFIED
UNSPECIFIEDAustralian Postgraduate AwardsUNSPECIFIED
UNSPECIFIEDMonash Graduate ScholarshipUNSPECIFIED

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