Azetidines and their applications in asymmetric catalysis

Milton, Joseph P.; Fossey, John S.

doi:10.1016/j.tet.2020.131767

Cited by 10 publications

(2 citation statements)

References 105 publications

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“…Lewis base catalysts, including various tertiary amines (1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 4-dimethylaminopyridine (DMAP), 1,4-diazabicyclo[2.2.2]octane (DABCO), Scheme 5. Plausible mechanism for the formation of furanones (2)(3)(4).…”

Section: Lewis Base Catalystsmentioning

confidence: 99%

“…Over the past two decades, reactions that rely on organocatalysts have emerged as important catalytic systems in asymmetric and conventional synthesis [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. The utilization of organocatalysts has garnered interest because they are robust, inexpensive, environmentally benign, and easily recoverable, among other advantageous characteristics.…”

Section: Introductionmentioning

confidence: 99%

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Regiodivergent Organocatalytic Reactions

et al. 2021

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Organocatalysts are abundantly used for various transformations, particularly to obtain highly enantio- and diastereomeric pure products by controlling the stereochemistry. These applications of organocatalysts have been the topic of several reviews. Organocatalysts have emerged as one of the very essential areas of research due to their mild reaction conditions, cost-effective nature, non-toxicity, and environmentally benign approach that obviates the need for transition metal catalysts and other toxic reagents. Various types of organocatalysts including amine catalysts, Brønsted acids, and Lewis bases such as N-heterocyclic carbene (NHC) catalysts, cinchona alkaloids, 4-dimethylaminopyridine (DMAP), and hydrogen bond-donating catalysts, have gained renewed interest because of their regioselectivity. In this review, we present recent advances in regiodivergent reactions that are governed by organocatalysts. Additionally, we briefly discuss the reaction pathways of achieving regiodivergent products by changes in conditions such as solvents, additives, or the temperature.

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Section: Lewis Base Catalystsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Regiodivergent Organocatalytic Reactions

et al. 2021

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Photoredox Catalytic Phosphite‐Mediated Deoxygenation of α‐Diketones Enables Wolff Rearrangement and Staudinger Synthesis of β‐Lactams

Hui

Guo

2021

Angewandte Chemie

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A novel visible‐light‐driven catalytic activation of C=O bonds by exploiting the photoredox chemistry of 1,3,2‐dioxaphospholes, readily accessible from α‐diketones and trialkyl phosphites, is reported. This mild and environmentally friendly strategy provides an unprecedented and efficient access to the Wolff rearrangement reaction which traditionally entails α‐diazoketones as precursors. The resulting ketenes could be precisely trapped by alcohols/thiols to give α‐aryl (thio)acetates and by imines to afford the valuable β‐lactams in up to 99 % yields.

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Enantioselective Iridium‐Catalyzed Reductive Coupling of Dienes with Oxetanones and N‐Acyl‐Azetidinones Mediated by 2‐Propanol

2022

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Cyclometallated iridium-PhanePhos complexes generated in situ from [Ir(cod)Cl] 2 and (R)-PhanePhos catalyze 2-propanol-mediated reductive couplings of 2-substituted dienes with oxetanone and Nacyl-azetidinones to form branched homoallylic oxetanols and azetidinols with excellent control of regio-and enantioselectivity without CÀ C cleavage of the strained ring via enantiotopic π-facial selection of transient allyliridium nucleophiles. This work represents the first systematic study of enantioselective additions to symmetric ketones.

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Azetidines and their applications in asymmetric catalysis

Cited by 10 publications

References 105 publications

Regiodivergent Organocatalytic Reactions

Regiodivergent Organocatalytic Reactions

Photoredox Catalytic Phosphite‐Mediated Deoxygenation of α‐Diketones Enables Wolff Rearrangement and Staudinger Synthesis of β‐Lactams

Enantioselective Iridium‐Catalyzed Reductive Coupling of Dienes with Oxetanones and N‐Acyl‐Azetidinones Mediated by 2‐Propanol

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