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A mass spectrometric method for rapidly assaying the chiral selectivities of the copper(I) complexes of C 2 ‐symmetric ligands
Author(s) -
Davis Mark C.,
Gronert Scott
Publication year - 2015
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.3643
Subject(s) - chemistry , imine , copper , oxazoline , reagent , mass spectrometry , ion trap , combinatorial chemistry , catalysis , metal , triple quadrupole mass spectrometer , organic chemistry , selected reaction monitoring , tandem mass spectrometry , chromatography
A gas‐phase method for rapidly assaying the enantioselectivity of metal‐centered catalysts is presented. It relies on gas‐phase equilibrium measurements in a quadrupole ion trap mass spectrometer. A group of well‐established C 2 ‐symmetric bis‐oxazoline copper(I) complexes was used to identify chiral probe reagents that are capable of profiling the quality of the asymmetric environment provided by the metal complex. The chiral probes were then applied to a wide variety of copper(I) bis‐di‐imine complexes. Complexes based on a BINAM backbone exhibited selectivities that were comparable to the bis‐oxazolines. Taking advantage of the mass selectivity capabilities of the ion trap mass spectrometer, the method was also applied to an un‐purified mix of copper(I) complexes derived from a combinatorial synthesis of bis‐di‐imine ligands. This approach holds promise as a rapid screening tool for potential chiral catalysts. Copyright © 2015 John Wiley & Sons, Ltd.