NDLI: Highly Enantioselective Fluorescent Recognition of Both Unfunctionalized and Functionalized Chiral Amines by a Facile Amide Formation from a Perfluoroalkyl Ketone

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Highly Enantioselective Fluorescent Recognition of Both Unfunctionalized and Functionalized Chiral Amines by a Facile Amide Formation from a Perfluoroalkyl Ketone

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Wang, Chao Pu, Lin Anbaei, Parastoo
Description	Author Affiliation: Wang C ( Department of Chemistry, University of Virginia, McCormick Rd, Charlottesville, VA, 22904, USA.); Anbaei P ( Department of Chemistry, University of Virginia, McCormick Rd, Charlottesville, VA, 22904, USA.); Pu L ( Department of Chemistry, University of Virginia, McCormick Rd, Charlottesville, VA, 22904, USA. lp6n@virginia.edu.)
Abstract	The $H_{8}BINOL-based$ perfluoroalkyl ketone (S)-2 is found to exhibit highly enantioselective fluorescent enhancements toward both unfunctionalized and functionalized chiral amines. It greatly expands the substrate scope of the corresponding BINOL-based sensor. A dramatic solvent effect was observed for the reaction of the amines with compound (S)-2. In DMF, cleavage of the perfluoroalkyl group of compound (S)-2 to form amides was observed but not in other solvents, such as methylene chloride, chloroform, THF, hexane, and perfluorohexane. Thus, the addition of another solvent, such as THF, can effectively quench the reaction of compound (S)-2 with amines in DMF to allow stable fluorescent measurement. This is the first example that the formation of strong amide bonds under very mild conditions is used for the enantioselective recognition of chiral amines. The mechanism of the reaction of compound (S)-2 with chiral amines is investigated by using various analytical methods including mass spectrometry as well as NMR and UV/Vis absorption spectroscopy.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	21
Volume Number	22
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2016-05-17
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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