Solvent free, fast and asymmetric Michael additions of ketones to nitroolefins using chiral pyrrolidine–pyridone conjugate bases as organocatalysts

Mahato, Chandan K.; Kundu, Mrinalkanti; Pramanik, Animesh

doi:10.1016/j.tetasy.2017.03.002

Cited by 20 publications

(20 citation statements)

References 53 publications

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“…This catalyst was tested in the addition of cyclohexanone to aryl and heteroaryl nitroolefins under neat conditions affording products 46 with good results, in terms of yields and stereoselectivities. Similar result was obtained when tetrahydro-4 H -pyran-2-one was used as reagent, while acyclic ketones, such as acetone or 2-butanone, gave poorer results [ 77 ].…”

Section: Carbon Nucleophilessupporting

confidence: 66%

Recent Advances in Asymmetric Organocatalyzed Conjugate Additions to Nitroalkenes

et al. 2017

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The asymmetric conjugate addition of carbon and heteroatom nucleophiles to nitroalkenes is a very interesting tool for the construction of highly functionalized synthetic building blocks. Thanks to the rapid development of asymmetric organocatalysis, significant progress has been made during the last years in achieving efficiently this process, concerning chiral organocatalysts, substrates and reaction conditions. This review surveys the advances in asymmetric organocatalytic conjugate addition reactions to α,β-unsaturated nitroalkenes developed between 2013 and early 2017.

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Section: Carbon Nucleophilessupporting

confidence: 66%

Recent Advances in Asymmetric Organocatalyzed Conjugate Additions to Nitroalkenes

et al. 2017

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“…The intermediate A was indicated that the pyridone component protects one side of the enamine and directs the nitroolefin to approach from the non-protected side where the hydrogen bonding stabilization was appeared by the pyridone ring (Scheme 6). [53] An admirable work was demonstrated by Szczesniak's group in 2017 for asymmetric Michael addition reaction of Scheme 8. Michael addition reaction of cyclohexane carboxaldehyde to nitroolefin.…”

Section: Scheme 7 Reaction Of Aldehydes To Nitroolefins Catalyzed By (S)-diphenylprolinol Tms Ethermentioning

confidence: 99%

Recent Advances in Organocatalytic Asymmetric Michael Addition Reactions to α, β‐Unsaturated Nitroolefins

et al. 2021

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An organocatalyzed asymmetric Michael addition reaction has been established as the most relevant and dynamic research area for the construction of chiral carbon‐carbon and carbon‐heteroatom bond. In the current scenario, rapid revolutions on asymmetric Michael addition to nitroolefins have been explored by taking advantage of newly developed chiral organocatalysts. Moreover, nitroolefins have proven as well‐known Michael acceptors for providing various structurally essential nitro‐functionalized frameworks. In addition to this, remarkable stereoselectivity has been achieved in this asymmetric process by following different mechanistic pathways that involve enamine, iminium ion intermediate formation and bifunctional H‐bonding interaction. So, we have discussed the recent advancements of organocatalytic Michael addition reactions to α, β‐unsaturated nitroolefins from the year 2016 to 2020.

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“…In 2017, Kundu's group introduced an inexpensive and novel class of chiral organocatalysts based on a conjugated pyrrolidine‐pyridine, 82 a – b , for the solvent‐free asymmetric Michael additions of ketones . It was noted that the carbonyl group of the pyridone ring provided H‐bonding with nitroolefin that played a critical role in the control of stereoselectivity in the Michael adducts.…”

Section: Solvent‐free Reactions In Asymmetric Catalysismentioning

confidence: 99%

“…In 2017, Kundu's group introduced an inexpensive and novel class of chiral organocatalysts based on a conjugated pyrrolidine-pyridine, 82 a-b, for the solvent-free asymmetric Michael additions of ketones. [82] It was noted that the carbonyl group of the pyridone ring provided H-bonding with nitroolefin that played a critical role in the control of stereoselectivity in the Michael adducts. When the model reaction was carried out in different aprotic solvents, such as toluene, THF, and DCE yield and enantioselectivity were comparable with the neat reaction albeit with prolonged reaction times, but in protic solvents such Scheme 56.…”

Section: Asymmetric Michael Reactionmentioning

confidence: 99%

Recent Advances in Solvent‐Free Asymmetric Catalysis

2019

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It is well‐known that solvent is one of the most important factors that affect chemical reactions. This factor is more noticeable and impressive in the asymmetric reactions where the effective interaction of reactants and the creation of a uniform chiral environment is necessary. Nevertheless, when reactions are carried out in the absence of solvent, some privileged advantages such as easy work up, short reaction time, lack of waste solvents, and following the green chemistry principles, are appeared. Therefore, according to the importance of asymmetric synthesis and green chemistry, solvent‐free asymmetric catalysis can act as a considerable and necessary subject in synthetic chemistry. In this review, we have a survey on the solvent‐free asymmetric synthesis by the use of either homogeneous or heterogeneous chiral catalysts.

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Solvent free, fast and asymmetric Michael additions of ketones to nitroolefins using chiral pyrrolidine–pyridone conjugate bases as organocatalysts

Cited by 20 publications

References 53 publications

Recent Advances in Asymmetric Organocatalyzed Conjugate Additions to Nitroalkenes

Recent Advances in Asymmetric Organocatalyzed Conjugate Additions to Nitroalkenes

Recent Advances in Organocatalytic Asymmetric Michael Addition Reactions to α, β‐Unsaturated Nitroolefins

Recent Advances in Solvent‐Free Asymmetric Catalysis

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