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  Functionality, Effectiveness, and Mechanistic Evaluation of a Multicatalyst-Promoted Reaction Sequence by Electrospray Ionization Mass Spectrometry

Alachraf, M. W., Wende, R. C., Schuler, S. M. M., Schreiner, P. R., & 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. doi:10.1002/chem.201502640.

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 Creators:
Alachraf, Mohammed Wasim1, Author           
Wende, Raffael C.2, Author
Schuler, Sören M. M.2, Author
Schreiner, Peter R.2, Author
Schrader, Wolfgang3, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Institute of Organic Chemistry, Justus-Liebig University Giessen, Heinrich-Buff-Ring 17, 35392 Giessen (Germany), ou_persistent22              
3Service Department Schrader (MS), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445629              

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Free keywords: electrospray ionization; mass spectrometry; organocatalysis; reaction mechanisms; structure elucidation
 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.

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Language(s): eng - English
 Dates: 2015-09-252015-11-02
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/chem.201502640
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: - Volume / Issue: 21 (45) Sequence Number: - Start / End Page: 16203 - 16208 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058