Journal article

Publication year: 2015

Pages: 16203-16208

Journal: Chemistry - A European Journal

Volume number: 21

Issue number: 45

DOI Link: https://doi.org/10.1002/chem.201502640

Publisher: Wiley

Abstract: 

A multicatalytic three‐step reaction consisting of epoxidation,
hydrolysis, and enantioselective monoacylation of cyclohexene was
studied by using mass spectrometry (MS). The reaction sequence was
carried out in a one‐pot reaction using a multicatalyst. All reaction
steps were thoroughly analyzed by electrospray ionization (ESI) MS (and
MS/MS), as well as high‐resolution MS for structure elucidation. These
studies allow us to shed light on the individual mode of action of each
catalytic moiety. Thus, we find that under the epoxidation conditions,
the catalytically active N‐methyl imidazole for the terminal
acylation step is partially deactivated through oxidation. This
observation helps to explain the lower efficiency of the catalyst in the
last step compared to the monoacylation performed separately. All
reactive intermediates and products of the reaction sequence, as well as
of the side‐reactions, were monitored, and we present a working
mechanism of the reaction.

Harvard Citation style: Alachraf, M., Wende, R., Schuler, S., Schreiner, P. and Schrader, W. (2015) Functionality, Effectiveness, and Mechanistic Evaluation of a Multicatalyst‐Promoted Reaction Sequence by Electrospray Ionization Mass Spectrometry, Chemistry - A European Journal, 21(45), pp. 16203-16208. https://doi.org/10.1002/chem.201502640

APA Citation style: Alachraf, M., Wende, R., Schuler, S., Schreiner, P., & Schrader, W. (2015). Functionality, Effectiveness, and Mechanistic Evaluation of a Multicatalyst‐Promoted Reaction Sequence by Electrospray Ionization Mass Spectrometry. Chemistry - A European Journal. 21(45), 16203-16208. https://doi.org/10.1002/chem.201502640