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Molecules 2015, 20(7), 11733-11764; doi:10.3390/molecules200711733

The Emergence of Quinone Methides in Asymmetric Organocatalysis

Department of Industrial Chemistry "Toso Montanari" and INSTM RU of Bologna, Alma Mater Studiorum, University of Bologna, V. Risorgimento 4, 40136 Bologna, Italy
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Academic Editor: Raquel Herrera
Received: 9 June 2015 / Revised: 17 June 2015 / Accepted: 19 June 2015 / Published: 25 June 2015
(This article belongs to the Collection Recent Advances in Organocatalysis)

Abstract

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. View Full-Text
Keywords: asymmetric catalysis; conjugate addition; cycloaddition; organocatalysis; phenol; quinone methide asymmetric catalysis; conjugate addition; cycloaddition; organocatalysis; phenol; quinone methide
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Caruana, L.; Fochi, M.; Bernardi, L. The Emergence of Quinone Methides in Asymmetric Organocatalysis. Molecules 2015, 20, 11733-11764.

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