Asymmetric aerobic decarboxylative Povarov reactions of <i>N</i>-aryl α-amino acids with methylenephthalimidines <i>via</i> cooperative photoredox and chiral Brønsted acid catalysis

Li, Jiangtao; Gu, Ziwei; Zhao, Xiaowei; Qiao, Baokun; Jiang, Zhiyong

doi:10.1039/c9cc07380a

Cited by 73 publications

(38 citation statements)

References 56 publications

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“…Followed by this efficient cooperative catalysis strategy, a series of valuable chiral isoindolin‐1‐ones 1 94 containing a 3,3‐spiro‐tetrahydroquinoline‐based stereocenter were well established by the same group (Scheme 58). [100] Similar to the above‐mentioned cascade process, the α ‐amino radical Int‐149 can be formed smoothly. A deprotonation then occurs to furnish the imine 195 from Int‐149 by the radical HO 2 .…”

Section: Asymmetric Reactions Catalyzed By Multi‐organocatalystsmentioning

confidence: 85%

Recent Advances in Asymmetric Organomulticatalysis

Xiao

Shao

et al. 2020

Adv Synth Catal

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Asymmetric multi‐catalysis, designed to mimic catalytic processes in nature, is a powerful instrument to fulfil fascinating transformations. As a result, this area of research has attracted considerable interests within chemistry communities. Although there are numerous reviews involving multi‐catalysis, reviews describing asymmetric organomulticatalysis remain rare. Taking into consideration that organocatalysts possess the superiorities of effortless availability, inexpensiveness, hypotoxicity, facile handling and hyposensitivity to moisture and oxygen, they have definite advantage in their own distinct modes of activation when utilized in multi‐catalytic reactions. Organomulticatalysis refers to the synthetic strategies of modular combination of organo‐catalyzed reactions into one synthetic operation with minimum workup or change in conditions. It is apparent that a variety reports utilizing the concept of enantioselective organomulticatalysis have substantially surfaced in the past few years. Hence, it is indispensable to succinctly present all such reports by means of disclosing the mechanistic analysis, as well as the challenges and issues associated in the development of the asymmetric catalytic system. Additionally, this review will introduce some of the unsettled conundrums and possible innovations in this field.

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Section: Asymmetric Reactions Catalyzed By Multi‐organocatalystsmentioning

confidence: 85%

Recent Advances in Asymmetric Organomulticatalysis

Xiao

Shao

et al. 2020

Adv Synth Catal

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“…Recently, Jiang with co‐authors [231] applied SPINOL‐derived Brønsted acid XXIXc in combination with dicyanopyrazine‐derived chromophore ( XXXII ) for the enantioselective aerobic decarboxylative Povarov reaction of N ‐aryl α‐ amino acids 221 with methylenephthalimidines 222 . The first step of this unusual transformation is visible light‐driven single‐electron‐transfer oxidation of the nitrogen atom in amino acid 221 with photoactivated photoredox catalyst XXXII* which triggers a cascade of deprotonation, proton transfer and decarboxylation reactions yielding the α‐ aminoalkyl radical species Int 21 (Scheme 82).…”

Section: Inverse Electron Demand Asymmetric Aza‐diels‐alder Reactionsmentioning

confidence: 99%

Catalytic Asymmetric Aza‐Diels‐Alder Reaction: Pivotal Milestones and Recent Applications to Synthesis of Nitrogen‐Containing Heterocycles

2021

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In this review, the pivotal achievements and recent advances in catalytic asymmetric aza‐DAR reported up to 2020 are retrospectively considered and their potency for enantioselective synthesis of useful chiral piperidine, quinoline, pyridazine, oxazine and oxadiazine derivatives and fused compounds of higher molecular complexity bearing these pharmacology‐relevant heterocyclic scaffolds is demonstrated. The reported data are systematized according both to key electron transfer modes (normal or invers electron demand reactions) and to main types of attainable heterocyclic products. Of significant attention are an analysis of activation strategies (complexation, enamine or enolate formation, H‐bonding, etc.) applicable to reactions with particular types of dienes and dienophiles and identification of plausible reaction pathways (either concerted or stepwise) over stereoselective cyclization processes. The review contains 310 references and 122 synthetic schemes.

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“…Subsequently, Jiang et al developed an enantioselective aerobic decarboxylative Povarov reaction of N-aryl α-amino acids 40 with methylenephthalimidines 64 in the presence of a dual catalysis system involving DPZ and SPINOL-CPA 53 (Scheme 15). 38 A range of important optically pure isoindolin-1-ones 65 that feature a 3,3-spiro-tetrahydroquinoline-based stereocentre were prepared in high yields, ees and drs. This work represents the first construction of the 3,3-spiro-six-membered ring of an isoindolin-1-ones through asymmetric catalysis.…”

Section: C-c and C-o Bond Formation Via Ionic-type Pathwaysmentioning

confidence: 99%