Aza-ortho-Quinone Methides as Reactive Intermediates: Generation and Utility in Contemporary Asymmetric Synthesis

Liao, Hsuan-Hung; Miñoza, Shinje; Lee, Shao-Chi; Rueping, Magnus

Aza-ortho-Quinone Methides as Reactive Intermediates: Generation and Utility in Contemporary Asymmetric Synthesis

Files

Chemistry A European J - 2022 - Liao - Aza‐ortho‐Quinone Methides as Reactive Intermediates Generation and Utility in_removed.pdf (3.68 MB)

Embargo End Date

2023-06-02

Type

Article

Authors

Liao, Hsuan-Hung
Miñoza, Shinje
Lee, Shao-Chi

Rueping, Magnus

KAUST Department

King 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

Date

2022-06-02

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 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.

Citation

Liao, 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

Acknowledgements

Dr. 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.