CF3‐Containing para‐Quinone Methides for Organic Synthesis. Issue 25 (30th March 2020)

• Record Type: Journal Article
• Authors: Winter, Michael; Schütz, Roman; Eitzinger, Andreas; Ofial, Armin R.; Waser, Mario
• Is Part Of: European journal of organic chemistry. Issue 25(2020)
• Page Start: 3812
• Page End: 3817
• Publication Date: 2020-03-30
• Subjects: Quinone methides -- Trifluoromethylation -- Electrophilicity -- Kinetics -- Phase‐transfer catalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000295
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A new family of CF3 ‐containing para ‐quinone methides (CF3 ‐QMs) was systematically investigated for its suitability in organic synthesis. Addition of different nucleophiles gives access to target molecules with a benzylic CF3 ‐containing stereogenic center straightforwardly. The electrophilicity parameter E of the prototypical CF3 ‐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. Abstract : Novel CF3 ‐containing para‐quinone methides were systematically investigated for their use in (asymmetric) transformations.