Aza‐Ortho‐Quinone Methides as Reactive Intermediates: Generation and Utility in Contemporary Asymmetric Synthesis. Issue 46 (27th June 2022)

• Record Type: Journal Article
• Authors: Liao, Hsuan‐Hung; Miñoza, Shinje; Lee, Shao‐Chi; Rueping, Magnus
• Is Part Of: Chemistry. Volume 28:Issue 46(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-06-27
• Subjects: asymmetric synthesis -- aza-o-QM -- organocatalysis -- transition-metals; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202201112
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The aza‐ ortho ‐quinone methide (aza‐ o ‐QM) chemistry has overwhelmingly progressed in the past few decades. This review aims to integrate various transition metal‐catalyzed and organocatalytic strategies in taming aza ‐o‐ QM intermediates, including the aza‐ ortho ‐vinylidene quinone methide (aza‐ o ‐VQM), aza‐ ortho ‐alkynyl quinone methide (aza‐ o ‐AQM), aza‐ para ‐quinone methide (aza‐ p ‐QM), and indole‐based aza‐ o ‐QM analog. These transient species are often utilized for the direct and enantioselective synthesis of complex (hetero)polycyclic or fused‐ring molecular scaffolds such as tetrahydroquinoline and indoline, among others, which are abundant in many natural products, bioactive compounds, and pharmaceuticals. Abstract : The aza‐ ortho ‐quinone methide (aza‐ o ‐QM) chemistry has been showing budding progress in the past years. Herein, the asymmetric catalysis involving these transient intermediates is highlighted, which was made possible by well‐designed catalysts as well as new aza‐ o ‐QM precursors/substrates.