Aza-ortho-Quinone Methides as Reactive Intermediates: Generation and Utility in Contemporary Asymmetric Synthesis
KAUST DepartmentKing Abdullah University of Science and Technology, KAUST Catalysis Center (KCC) SAUDI ARABIA
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Chemical Science Program
Embargo End Date2023-06-02
Permanent link to this recordhttp://hdl.handle.net/10754/678592
MetadataShow full item record
AbstractThe 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 its the aza- para -quinone methide (aza- p -QM), aza- ortho -vinylidene quinone methide (aza- o -VQM), aza- ortho -alkynyl quinone methide (aza- o -AQM), and indole-based aza- o -QM analogs. 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.
CitationLiao, H.-H., Miñoza, S., Lee, S.-C., & Rueping, M. (2022). Aza-ortho-Quinone Methides as Reactive Intermediates: Generation and Utility in Contemporary Asymmetric Synthesis. Chemistry – A European Journal. Portico. https://doi.org/10.1002/chem.202201112
SponsorsDr. Hsuan-HungLiao expresses his gratitude to the Young Scholar Fellowship Program of Ministry of Science and Technology (MOST110-2636-M-110-003) and Yushan Young Scholar Program of Ministry of Education (MOE) in Taiwan for their financial support. Shinje Miñoza also thanks National Sun Yat-sen University(NSYSU) Scholarship. The authors are thankful for Heng-Bo Lin (NSYSU), Joshua Andrew P. Nillama (Mindanao State University –Iligan Institute of Technology), and Ivy L. Librando (University of Lisbon) for proofreading this review.
JournalChemistry – A European Journal
- Applications of ortho-quinone methide intermediates in catalysis and asymmetric synthesis.
- Authors: Pathak TP, Sigman MS
- Issue date: 2011 Nov 18
- The Emergence of Quinone Methides in Asymmetric Organocatalysis.
- Authors: Caruana L, Fochi M, Bernardi L
- Issue date: 2015 Jun 25
- Aza-ortho-Quinone Methide and Its Conjugated Acid: Reactivity, Stability and Acidity.
- Authors: Wu TH, Su ZS, Sung R, Sung K
- Issue date: 2020 Feb 17
- Multicomponent Reactions (MCRs) with o-Quinone Methides.
- Authors: Martins MTM, Dias FRF, de Moraes RSM, da Silva MFV, Lucio KR, D'Oliveira Góes K, do Nascimento PA, da Silva ASS, Ferreira VF, Cunha AC
- Issue date: 2022 Mar
- An Isolable Vinylidene ortho-Quinone Methide: Synthesis, Structure and Reactivity.
- Authors: Liu H, Li K, Huang S, Yan H
- Issue date: 2022 May 9