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Asymmetric Morita-Baylis-Hillman Reaction: Catalyst Development and Mechanistic Insights Based on Mass Spectrometric Back-Reaction Screening.
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 3700228
Author(s) Isenegger, Patrick G; Bächle, Florian; Pfaltz, Andreas
Author(s) at UniBasel Pfaltz, Andreas
Isenegger, Patrick
Year 2016
Title Asymmetric Morita-Baylis-Hillman Reaction: Catalyst Development and Mechanistic Insights Based on Mass Spectrometric Back-Reaction Screening.
Journal Chemistry - A European Journal
Volume 22
Number 49
Pages / Article-Number 17595-17599
Abstract An efficient protocol for the evaluation of catalysts for the asymmetric Morita-Baylis-Hillman (MBH) reaction was developed. By mass spectrometric back-reaction screening of quasi-enantiomeric MBH products, an efficient bifunctional phosphine catalyst was identified that outperforms literature-known catalysts in the MBH reaction of methyl acrylate with aldehydes. The close match between the selectivities measured for the forward and back reaction and kinetic measurements provided strong evidence that the aldol step and not the subsequent proton transfer is rate- and enantioselectivity-determining.
Publisher Wiley
ISSN/ISBN 0947-6539 ; 1521-3765
edoc-URL http://edoc.unibas.ch/52228/
Full Text on edoc No
Digital Object Identifier DOI 10.1002/chem.201604616
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/27775188
ISI-Number WOS:000388471700017
Document type (ISI) Article
 
   

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