Enantioselective Synthesis of Chiral Pyrazolo[3,4‐d]azepin‐7(2H,4H,8H)‐one Derivatives through a Sequential Michael Addition and Reductive Ring‐Closing Strategy

Xu, Yan; Sun, Panpan; Song, Qi; Lai, Xiaoyan; Liu, Wei; Tao, Xia; Huang, Yiyong; Shen, Yi

doi:10.1002/ejoc.201700443

Cited by 9 publications

(1 citation statement)

References 34 publications

(16 reference statements)

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“…Both tetrahydropyrano[2,3- c ]pyrazole ( II ) and its analogue ( III ) serve as fungicides . In this regard, several catalytic asymmetric reactions of pyrazolones with different Michael acceptors, such as nitro-alkenes, carbonyl compounds, maleimides, and isatylidene malononitriles, were developed in the past few years, affording various optically active pyrazolone derivatives. Among them, organocatalysts proved to be very powerful and versatile catalysts for achieving these transformations, albeit with its relatively large catalyst loading.…”

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confidence: 99%

Chiral-at-Metal Rh(III) Complex-Catalyzed Michael Addition of Pyrazolones with α,β-Unsaturated 2-Acyl Imidazoles

Wan

Kang

2018

Org. Lett.

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An efficient enantioselective conjugate addition of pyrazolones with α,β-unsaturated 2-acyl imidazoles catalyzed by chiral-at-metal rhodium complex is reported. The corresponding adducts were obtained in good yields (85%-96%) with excellent enantioselectivities (up to >99%). This protocol exhibits extraordinary reactivity, because of the fact that a complex with as little as 0.05 mol % Rh(III) can catalyze the title reaction on a gram-scale with excellent enantioselectivity.

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confidence: 99%

Chiral-at-Metal Rh(III) Complex-Catalyzed Michael Addition of Pyrazolones with α,β-Unsaturated 2-Acyl Imidazoles

Wan

Kang

2018

Org. Lett.

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Synthesis of Pyrrolidones and Caprolactams by Intramolecular Cyclization of Linear Precursors

Arthur

Chenault

2021

Handbook of Pyrrolidone and Caprolactam Based Materials

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Pyrrolidones and caprolactams are important molecules, serving functions ranging from their use as solvents and surfactants to their occurrence in natural products and drugs. This chapter is devoted to the synthesis of pyrrolidones and caprolactams by intramolecular ring‐forming reactions. Perhaps the simplest heterolytic cyclization to envision is the attack of an amine group onto a carboxylic acid derivative, forming the amide C–N linkage. Pyrrolidones can be created by carboxamide radical cyclization onto an alkene. Amidyl radicals can activate remote C–H bonds to cyclization. The chapter presents the synthesis of pyrrolidones and caprolactams by homolytic (radical), carbene insertion and metathetic cyclization reactions. Carbenoid attack on an electron‐rich aromatic ring competes favorably with insertion into alkane C–H. Olefin metathesis is a metal‐catalyzed reaction that entails the redistribution of alkene carbons by the scission and regeneration of carbon–carbon double bonds.

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Stereospecific Synthesis of Fluorinated Pyrazolidinones and Isoxazolidines via a Catalyst‐Free 1,3‐Dipolar Cycloaddition of β‐Fluoroalkylated α,β‐Unsaturated 2‐Pyridylsulfones

et al. 2018

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A highly atom-economic, regio-and stereospecific synthesis of fluorinated pyrazolidinones and isoxazolidines is disclosed under catalyst-and additive-free mild conditions. The diastereoselectivity with different type of 1,3-dipoles is elucidated by using DFT calculations in CH 3 CN. Furthermore, a reaction using a chiral azomethine imine, a gram-scale synthesis, and a reductive desulfonylation are also presented.

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Enantioselective Synthesis of Chiral Pyrazolo[3,4‐d]azepin‐7(2H,4H,8H)‐one Derivatives through a Sequential Michael Addition and Reductive Ring‐Closing Strategy

Cited by 9 publications

References 34 publications

Chiral-at-Metal Rh(III) Complex-Catalyzed Michael Addition of Pyrazolones with α,β-Unsaturated 2-Acyl Imidazoles

Chiral-at-Metal Rh(III) Complex-Catalyzed Michael Addition of Pyrazolones with α,β-Unsaturated 2-Acyl Imidazoles

Synthesis of Pyrrolidones and Caprolactams by Intramolecular Cyclization of Linear Precursors

Stereospecific Synthesis of Fluorinated Pyrazolidinones and Isoxazolidines via a Catalyst‐Free 1,3‐Dipolar Cycloaddition of β‐Fluoroalkylated α,β‐Unsaturated 2‐Pyridylsulfones

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