Asymmetric Organocatalyzed Friedel-Crafts Reaction of Trihaloacetaldehydes and Phenols
| Authors | |
|---|---|
| Year of publication | 2022 |
| Type | Article in Periodical |
| Magazine / Source | Advanced Synthesis and Catalysis |
| MU Faculty or unit | |
| 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. |
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