Chiral bipyridine-annulated bicyclo[3.3.1]nonane N-oxide organocatalysts for stereoselective allylation and hydrosilylation reactions

Žeimytė, Simona; Stončius, Sigitas

doi:10.1016/j.tet.2020.131831

Cited by 7 publications

(4 citation statements)

References 56 publications

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“…The synthesis of chiral C 2 -symmetric bis-bipyridine 58 was reported by Stončius starting from unsaturated ketone 57 (Scheme 27). 56 It involved bi-directional annulation of enantioenriched bicyclo[3.3.1]nonane-2,6-dione (56) in the presence of hydroxylamine hydrochloride as a source of nitrogen. The yields varied from 22-69% depending on the nature of the aromatic substituent in 57.…”

Section: Other Methods For the Synthesis Of 22′-bipyridinesmentioning

confidence: 99%

Recent Advances in the Synthesis of 2,2′-Bipyridines and Their Derivatives

Рубцов

Malkov

2021

Synthesis

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The sustained interest in the synthesis of new analogues of 2,2′-bipyridines is supported by the importance of compounds featuring bipyridine core in diverse areas of chemical, biomedical and materials research, which is relayed into the development of new approaches and the expansion of existing synthetic methods. This short review covers advances in the synthesis of 2,2′-bipyridines, including both the synthesis of compounds with a given substitution pattern and the development of new methods for assembling the bipyridine core. Special attention is directed toward the use of pyridine N-oxides and metal-free protocols to facilitate the formation of bipyridines. This short review focuses primarily on reports published in the last 5–6 years.1 Introduction2 Ullmann-Type Homocoupling Reactions3 Cross-Coupling Reactions in the Synthesis of Bipyridines4 Coupling Reactions Employing Pyridine N-Oxides5 Other Methods for the Synthesis of 2,2′-Bipyridines6 Conclusions and Outlook

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Section: Other Methods For the Synthesis Of 22′-bipyridinesmentioning

confidence: 99%

Recent Advances in the Synthesis of 2,2′-Bipyridines and Their Derivatives

Рубцов

Malkov

2021

Synthesis

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“…Additional references are cited within the Supporting Information. [61][62][63][64][65][66][67][68][69][70][71][72][73][74][75][76][77][78]…”

Section: Supporting Informationmentioning

confidence: 99%

Autocatalytic Green Synthesis of Imines in Traceless Medium

et al. 2023

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For the first time, condensations of amines with carbonyl compounds have been performed in supercritical carbon dioxide (sc‐CO2). The reactions with aldehydes or active ketones proceed at moderate temperatures (35–55 °C) without use of external catalysts. The process is autocatalytic: it is accelerated by the carbonic acid generated in situ by interaction between the released water and the CO2 medium. The imine products were obtained in high yields in a crystalline form and did not require further purification. The one‐pot transfer hydrogenation and [4+2] cycloaddition reactions performed in the CO2 medium have uncovered attractive prospects for facile green synthesis of more complex and valuable compounds from the generated in situ imine products.

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“…Since Matsumura's seminal work, that employed N-formylproline-derived catalysts [33,34], and the milestone achieved by Malkov and Kočovský with their N-methyl-L -valine-based catalysts [35][36][37], numerous chiral Lewis-base catalysts have been reported for the asymmetric hydrosilylation of ketimines with trichlorosilane (selected reviews; [30][31][32], selected references; [38][39][40][41][42][43][44][45]). While the majority of these catalysts are amide-based Lewis-bases, other kinds of Lewis-bases are also reported, which includes pyridine N-oxides (selected references; [46][47][48][49][50][51]), phosphine oxides (selected references; [52][53][54]), and sulfinamides (selected references; [55,56]). Despite a plethora of reports in this area, the Lewis-base-catalyzed trichlorosilane-mediated reduction of ketimines currently remains limited to N-aryl and alkyl protected ones (Scheme 1, Equation ( 2)).…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Evaluation of 3,3′-Triazolyl Biisoquinoline N,N′-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane

Sun

Jarvis

et al. 2021

Catalysts

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A new class of axial-chiral biisoquinoline N,N′-dioxides was evaluated as catalysts for the enantioselective hydrosilylation of acyl hydrazones with trichlorosilane. While these catalysts provided poor to moderate reactivity and enantioselectivity, this study represents the first example of the organocatalytic asymmetric reduction of acyl hydrazones. In addition, the structures and energies of two possible diastereomeric catalyst–trichlorosilane complexes (2a–HSiCl3) were analyzed using density functional theory calculations.

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Chiral bipyridine-annulated bicyclo[3.3.1]nonane N-oxide organocatalysts for stereoselective allylation and hydrosilylation reactions

Cited by 7 publications

References 56 publications

Recent Advances in the Synthesis of 2,2′-Bipyridines and Their Derivatives

Recent Advances in the Synthesis of 2,2′-Bipyridines and Their Derivatives

Autocatalytic Green Synthesis of Imines in Traceless Medium

Evaluation of 3,3′-Triazolyl Biisoquinoline N,N′-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane

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