Asymmetric Organocatalyzed Friedel-Crafts Reaction of Trihaloacetaldehydes and Phenols

Warning

This publication doesn't include Faculty of Education. It includes Faculty of Pharmacy. Official publication website can be found on muni.cz.
Authors

ŠVESTKA David OTEVŘEL Jan BOBÁĽ Pavel

Year of publication 2022
Type Article in Periodical
Magazine / Source Advanced Synthesis and Catalysis
MU Faculty or unit

Faculty of Pharmacy

Citation
Web https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202200180
Doi http://dx.doi.org/10.1002/adsc.202200180
Keywords Friedel-Crafts; Hydrogen-Bond Catalysis; Phenol; Trihaloacetaldehyde; Cinchona alkaloids
Attached files
Description Herein we report the asymmetric organocatalyzed method for the Friedel-Crafts reaction between activated phenols and trihaloacetaldehydes. A three-phase screening including 41 compounds was employed to identify a catalyst structure based on 3,5-dinitrobenzamide of 9-amino-epi-cinchonidine as the lead catalytic molecule. Under the optimized reaction conditions, the above catalyst offered trihalohydroxyalkylated adducts in yields ranging from 26 to 92% and enantiomeric ratios within 69:31-99:1. The reaction scope was determined on 29 entries and several follow-up transformations of the enantioenriched products were accomplished.
Related projects:

You are running an old browser version. We recommend updating your browser to its latest version.