Fluorous‐Phase‐Based Chiral Assay with Circular Dichroism Spectroscopy. Issue 11 (20th March 2017)

• Record Type: Journal Article
• Authors: Xiao, Meng; Yu, Shanshan; Chen, Liming; Huang, Zeng; Wen, Kaili; Xu, Yimang; Zhao, Feng; Yu, Xiaoqi; Pu, Lin
• Is Part Of: European journal of organic chemistry. Issue 11(2017)
• Page Start: 1413
• Page End: 1417
• Publication Date: 2017-03-20
• Subjects: Analytical methods -- Sensors -- Perfluorinated solvents -- Circular dichroism -- Chirality; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601643
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A highly fluorinated molecular probe made of a salicylaldehyde derivative is designed and synthesized for the detection of chiral amines in the fluorous phase. When treated with various chiral amines in a fluorous solvent (perfluorohexyl ethanol), this probe shows intense CD signals at wavelengths greater than 400 nm, which has been used to determine the enantiomeric composition of chiral amines, amino alcohols, and amino acids. This is the first example of CD recognition of chiral compounds that is conducted in the fluorous phase. The approach could greatly reduce the undesired interference in the direct assay of asymmetric reactions and catalytic processes. Abstract : A highly fluorinated sensor is found to exhibit intense circular dichroism signals in the presence of chiral amines, amino alcohols, and amino acids in a fluorous solvent. This allows direct measurement of the enantiomeric excess of the substrates in the fluorous phase.