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 . 130591. doi:10.1016/j.tet.2019.130591 (In Press)

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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
Divisions:	Faculty of Science > Chemistry
Journal or Publication Title:	Tetrahedron
Publisher:	Pergamon
ISSN:	0040-4020
Official Date:	9 September 2019
Dates:	Date Event 9 September 2019 Available 2 September 2019 Accepted
Date of first compliant deposit:	13 September 2019
Article Number:	130591
DOI:	10.1016/j.tet.2019.130591
Status:	Peer Reviewed
Publication Status:	In Press
Access rights to Published version:	Restricted or Subscription Access

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