The Emergence of Quinone Methides in Asymmetric Organocatalysis

• Main Authors: Lorenzo Caruana, Mariafrancesca Fochi, Luca Bernardi
• Format: Article
• Language: English
• Published: MDPI AG 2015-06-01
• Series: Molecules
• Subjects: asymmetric catalysis; conjugate addition; cycloaddition; organocatalysis; phenol; quinone methide
• Online Access: http://www.mdpi.com/1420-3049/20/7/11733

Quinone methides (QMs) are highly reactive compounds that have been defined as “elusive” intermediates, or even as a “synthetic enigma” in organic chemistry. Indeed, there were just a handful of examples of their utilization in catalytic asymmetric settings until some years ago. This review collects organocatalytic asymmetric reactions that employ QMs as substrates and intermediates, from the early examples, mostly based on stabilized QMs bearing specific substitution patterns, to more recent contributions, which have dramatically expanded the scope of QM chemistry. In fact, it was only very recently that the generation of QMs in situ through strategies compatible with organocatalytic methodologies has been realized. This tactic has finally opened the gate to the full exploitation of these unstable intermediates, leading to a series of remarkable disclosures. Several types of synthetically powerful asymmetric addition and cycloaddition reactions, applicable to a broad range of QMs, are now available.