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

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

doi:10.1002/chem.202201112

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

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

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

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.

Original language	English (US)
Journal	Chemistry – A European Journal
DOIs	https://doi.org/10.1002/chem.202201112
State	Published - Jun 2 2022

Bibliographical note

KAUST Repository Item: Exported on 2022-06-06
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.

ASJC Scopus subject areas

General Chemistry

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10.1002/chem.202201112

https://repository.kaust.edu.sa/bitstream/10754/678592/1/Chemistry%20A%20European%20J%20-%202022%20-%20Liao%20-%20Aza%e2%80%90ortho%e2%80%90Quinone%20Methides%20as%20Reactive%20Intermediates%20%20Generation%20and%20Utility%20in_removed.pdf

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

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.",

author = "Hsuan-Hung Liao and Shinje Mi{\~n}oza and Shao-Chi Lee and Magnus Rueping",

note = "KAUST Repository Item: Exported on 2022-06-06 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 Mi{\~n}oza 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.",

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AU - Rueping, Magnus

N1 - KAUST Repository Item: Exported on 2022-06-06 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.

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N2 - 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.

AB - 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.

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

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