Proline bulky substituents consecutively act as steric hindrances and directing groups in a Michael/Conia-ene cascade reaction under synergistic catalysis

Putatunda, Salil; Alegre‐Requena, Juan V.; Meazza, Marta; Franc, Michael; Rohal'ová, Dominika; Vemuri, Pooja Y.; Cı́sařová, Ivana; Herrera, Raquel P.; Rios, Ramón; Veselý, Ján

doi:10.1039/c8sc05258a

Cited by 30 publications

(15 citation statements)

References 48 publications

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“…The general applicability of this protocol was investigated and it was found that the reaction proceeds smoothly for enals 5 and pyrazolones 22 having different electronic and steric effects (Scheme 14). [45] In the same year, this group disclosed the synthesis of spiroazlactone (spirooxazolone) derivatives 25 via asymmetric cyclization of enals 5 with vinylcyclopropane azlactones 24. The reaction is efficiently catalyzed by the combination of tris(dibenzylideneacetone) dipalladium(0) and chiral secondary amines.…”

Section: Combining Pd and Aminocatalystsmentioning

confidence: 99%

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Combined Power of Organo‐ and Transition Metal Catalysis in Organic Synthesis

et al. 2022

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The combination of organocatalysis with transition metal catalysis is an emerging research area for the scientific community. Various unprecedented transformations that are otherwise inaccessible by individual catalytic systems can be achieved with good efficiency and stereocontrolled manner by this dual-catalytic strategy. This Review presents a detailed discussion on the recent advances in dual catalytic systems combining organocatalysis and transition metal catalysis, covering the literature of the last five years. A wide variety of combinations of transition metals with organocatalysts including aminocatalysts, such as secondary amines and more recent primary amines, Brønsted acid catalysts, especially phosphoric acids based on the chiral BINOL scaffold and N-heterocyclic carbene catalysts, are discussed. Considering the great contribution of this domain to organic synthesis, the present and future potential of this new and exciting research field is highlighted.

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Section: Combining Pd and Aminocatalystsmentioning

confidence: 99%

Section: Combining Aminocatalysis and Transition Metal Catalysismentioning

confidence: 99%

Combined Power of Organo‐ and Transition Metal Catalysis in Organic Synthesis

et al. 2022

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“…The corresponding tandem products were in high yields and with excellent enantioselectivities [80]. Silyl ethers of diarylprolinol were also used in the highly stereoselective synthesis of spiro pyrazolones via Michael/Conia-ene cascade reaction [82] and in the synthesis of biaryl atropoisomers via domino Michael-Henry reaction affording the substituted nitrocyclohexanecarbaldehydes [83].…”

Section: Asymmetric Michael Reactionsmentioning

confidence: 99%

Recent Advances in Selected Asymmetric Reactions Promoted by Chiral Catalysts: Cyclopropanations, Friedel–Crafts, Mannich, Michael and Other Zinc-Mediated Processes—An Update

2021

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The main purpose of this review article is to present selected asymmetric synthesis reactions in which chemical and stereochemical outcomes are dependent on the use of an appropriate chiral catalyst. Optically pure or enantiomerically enriched products of such transformations may find further applications in various fields. Among an extremely wide variety of asymmetric reactions catalyzed by chiral systems, we are interested in: asymmetric cyclopropanation, Friedel–Crafts reaction, Mannich and Michael reaction, and other stereoselective processes conducted in the presence of zinc ions. This paper describes the achievements of the above-mentioned asymmetric transformations in the last three years. The choice of reactions is related to the research that has been carried out in our laboratory for many years.

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“…In 2019, Herrera, Rios, Veselý, and co-workers described a tandem reaction of 4-propargylpyrazolones with ,-unsaturated aldehydes (Scheme 27). 58 In particular, this example consists of a Michael addition catalyzed by the Jørgensen-Hayashi catalyst 59 followed by a Pd(II)-catalyzed Conia-ene cyclization. The corresponding spirocyclic products were obtained in low to moderate diastereoselectivities (up to 5.6:1 dr), low to high yields (up to 93%), and excellent enantiomeric excess (up to 96% ee).…”

Section: Asymmetric Synthesis Of Chiral Spiropyrazolones Bearing a Fumentioning

confidence: 99%

Recent Advances in Catalytic Enantioselective Synthesis of Pyrazolones with a Tetrasubstituted Stereogenic Center at the 4-Position

Carceller‐Ferrer¹,

Blay²,

Pedro³

et al. 2020

Synthesis

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Pyrazolone [2,4-dihydro-3H-pyrazol-4-one] represents one of the most important five-membered nitrogen heterocycles which is present in numerous pharmaceutical drugs and molecules with biological activity. Recently, many catalytic methodologies for the asymmetric synthesis of chiral pyrazolones have been established with great success, specially, for the synthesis of pyrazolones bearing a tetrasubstituted stereocenter at C-4. This review summarizes these excellent research studies since 2018, including representative examples and some mechanistic pathways explaining the observed stereochemistry.1 Introduction2 Catalytic Enantioselective Synthesis of Chiral Pyrazolones with a Full Carbon Tetrasubstituted Stereocenter at C-43 Catalytic Enantioselective Synthesis of Chiral Pyrazolones with a Quaternary Carbon Stereocenter at C-4 bearing a Heteroatom4 Catalytic Enantioselective Synthesis of Chiral Spiropyrazolones5 Conclusion

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Proline bulky substituents consecutively act as steric hindrances and directing groups in a Michael/Conia-ene cascade reaction under synergistic catalysis

Abstract: In this study, we report a highly stereoselective and versatile synthesis of spiro pyrazolones, promising motifs that are being employed as pharmacophores.

Cited by 30 publications

References 48 publications

Combined Power of Organo‐ and Transition Metal Catalysis in Organic Synthesis

Combined Power of Organo‐ and Transition Metal Catalysis in Organic Synthesis

Recent Advances in Selected Asymmetric Reactions Promoted by Chiral Catalysts: Cyclopropanations, Friedel–Crafts, Mannich, Michael and Other Zinc-Mediated Processes—An Update

Recent Advances in Catalytic Enantioselective Synthesis of Pyrazolones with a Tetrasubstituted Stereogenic Center at the 4-Position

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