107474-78-2Relevant articles and documents
Separation of Amino Acid Enantiomers and Chiral Amines Using Precolumn Derivatization with (+)-1-(9-Fluorenyl)ethyl Chloroformate and Reversed-Phase Liquid Chromatography
Einarsson, Stefan,Josefsson, Bjoern,Moeller, Per,Sanchez, Domingo
, p. 1191 - 1195 (1987)
A new chiral reagent (+)-1-(9-fluorenyl)ethyl chloroformate (FLEC) was synthesized for separation of amino acid enentiomers and optically active amines.Highly fluorescent diastereomers of amino acids were obtained without racemization within 4 min at room temperature.The derivatives have favorable chromatographic properties, which is demonstrated by a reversed-phase separation of the D and L form of 17 primary amino acids in a single run.The secondary amino acids were resolved separately at a lower pH and can be determined without interferences from primary amino acids.The stability of the derivatives permitted confirmation studies with gas chromatography-mass spectrometry.
(S)-(?)-Fluorenylethylchloroformate (FLEC); preparation using asymmetric transfer hydrogenation and application to the analysis and resolution of amines
Amin, Mohammad A.,Camerino, Michelle A.,Mountford, Simon J.,Ma, Xiao,Manallack, David T.,Chalmers, David K.,Wills, Martin,Thompson, Philip E.
, (2019/09/19)
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.
(+)-Fluorenylethylchloroformate (FLEC)-improved synthesis for application in chiral analysis and peptidomimetic synthesis
Camerino, Michelle A.,Chalmers, David K.,Thompson, Philip E.
, p. 2571 - 2573 (2013/06/05)
An efficient synthesis of the enantiomers of fluorenylethylchloroformate (FLEC) has been achieved that allows the routine application of the reagent for the resolution of chiral amines including unusual amino acids. The utility of the fluorenylethoxycarbonyl (Feoc) group as a chiral Fmoc equivalent, for combined resolution and protection of amino acids, in solid phase peptide synthesis is also shown.
Solvent-promoted E2 reaction competing with SN2 reaction and stepwise solvolytic elimination and substitution reactions
Meng, Qingshui,Thibblin, Alf
, p. 9399 - 9407 (2007/10/03)
Solvolysis of 9-(1-X-ethyl)fluorene (1-X, X = I, Br, Cl, OTs, or OBs) in 25 vol % acetonitrile in water gives the elimination products 9-(1-ethylidene)fluorene (3) and 9-vinylfluorene (2) and the substitution products 9-(1-hydroxyethyl)fluorene (1-OH) and