CF<sub>3</sub>‐Containing <i>para</i>‐Quinone Methides for Organic Synthesis
Michael Winter, Roman Schütz, Andreas Eitzinger, Armin R. Ofial, Mario Waser
Abstract
A new family of CF 3 ‐containing para ‐quinone methides (CF 3 ‐QMs) was systematically investigated for its suitability in organic synthesis. Addition of different nucleophiles gives access to target molecules with a benzylic CF 3 ‐containing stereogenic center straightforwardly. The electrophilicity parameter E of the prototypical CF 3 ‐QM 2,6‐di‐ tert ‐butyl‐4‐(2,2,2‐trifluoroethylidene)cyclohexa‐2,5‐dien‐1‐one was determined to be –11.68 according to the Mayr scale, making it one of the most reactive quinone methides known so far.
Topics & Concepts
ChemistryElectrophileQuinoneStereocenterNucleophileOrganic synthesisOrganic moleculesStereochemistryMoleculeOrganic chemistryMedicinal chemistryEnantioselective synthesisCatalysisSynthesis of Indole DerivativesSulfur-Based Synthesis TechniquesChemical Synthesis and Reactions