Synthesis of Chiral 4-(ω-Hydroxyalkyl)pyrazolidin-3-ones by Ring-Chain Transformation of α-Alkylidenelactones with Hydrazines

Otto, Andreas; Ziemer, Burkhard; Liebscher, Jürgen

doi:10.1002/(sici)1099-0690(199811)1998:11<2667::aid-ejoc2667>3.0.co;2-r

Eur. J. Org. Chem.

1998

DOI: 10.1002/(sici)1099-0690(199811)1998:11<2667::aid-ejoc2667>3.0.co;2-r

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Synthesis of Chiral 4-(ω-Hydroxyalkyl)pyrazolidin-3-ones by Ring-Chain Transformation of α-Alkylidenelactones with Hydrazines

Andreas Otto

Burkhard Ziemer

Jürgen Liebscher

Abstract: Enantiopure α‐alkylidenelactones 7 were prepared by a Wittig reaction from α‐bromolactones 4 and chiral aldehydes 6. Compounds 7 react with hydrazines 9 by stereoselective Michael‐like addition and ring–chain transformation affording optically active 4‐(ω‐hydroxyalkyl)pyrazolidin‐3‐ones 11.

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Cited by 16 publications

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CO₂‐Activation for γ‐Butyrolactones and Its Application in the Total Synthesis of (±)‐Heteroplexisolide E

Li¹,

Ma²

2012

Chemistry An Asian Journal

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An efficient nickel(0)-catalyzed highly regio- and stereoselective hydrocarboxylation of homopropargylic alcohols with ZnEt(2) in the presence of CO(2) (1 atm, balloon) to synthesize α-alkylidene-γ-butyrolactones is described. The catalyst is highly active and can be applied for the synthesis of (optically active) mono- or bicyclic α-alkylidene-γ-butyrolactones with excellent regio- and stereoselectivity and good functional group tolerance. The potential of the reaction has been demonstrated in the first synthesis of (±)-heteroplexisolide E.

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CO₂‐Activation for γ‐Butyrolactones and Its Application in the Total Synthesis of (±)‐Heteroplexisolide E

Li¹,

Ma²

2012

Chemistry An Asian Journal

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ChemInform Abstract: Synthesis of Chiral 4‐(ω‐Hydroxyalkyl)pyrazolidin‐3‐ones by Ring‐Chain Transformation of α‐Alkylidenelactones with Hydrazines.

1999

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Synthesis and Transformations of Novel L‐Phenylalanine Derived Pyrazolidin‐3‐ones

et al. 2013

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A simple and straightforward four-step synthesis of novel diastereomeric L-phenylalanine-derived pyrazolidin-3-ones is described. The absolute configuration of the novel C(5) stereogenic centre has been unambiguously determined by single crystal X-ray analysis and via chemical interconversions. A series of novel thiourea derived pyrazolidinones have been prepared and tested as potential organocatalysts. N(1) un-substituted pyrazolidinones can be used for the construction of a novel type of bicyclic heterocycles and other selective derivatizations.

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Synthesis of Chiral 4-(ω-Hydroxyalkyl)pyrazolidin-3-ones by Ring-Chain Transformation of α-Alkylidenelactones with Hydrazines

Cited by 16 publications

References 27 publications

CO₂‐Activation for γ‐Butyrolactones and Its Application in the Total Synthesis of (±)‐Heteroplexisolide E

CO₂‐Activation for γ‐Butyrolactones and Its Application in the Total Synthesis of (±)‐Heteroplexisolide E

ChemInform Abstract: Synthesis of Chiral 4‐(ω‐Hydroxyalkyl)pyrazolidin‐3‐ones by Ring‐Chain Transformation of α‐Alkylidenelactones with Hydrazines.

Synthesis and Transformations of Novel L‐Phenylalanine Derived Pyrazolidin‐3‐ones

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Synthesis of Chiral 4-(ω-Hydroxyalkyl)pyrazolidin-3-ones by Ring-Chain Transformation of α-Alkylidenelactones with Hydrazines

Cited by 16 publications

References 27 publications

CO2‐Activation for γ‐Butyrolactones and Its Application in the Total Synthesis of (±)‐Heteroplexisolide E

CO2‐Activation for γ‐Butyrolactones and Its Application in the Total Synthesis of (±)‐Heteroplexisolide E

ChemInform Abstract: Synthesis of Chiral 4‐(ω‐Hydroxyalkyl)pyrazolidin‐3‐ones by Ring‐Chain Transformation of α‐Alkylidenelactones with Hydrazines.

Synthesis and Transformations of Novel L‐Phenylalanine Derived Pyrazolidin‐3‐ones

Contact Info

Product

Resources

About

CO₂‐Activation for γ‐Butyrolactones and Its Application in the Total Synthesis of (±)‐Heteroplexisolide E

CO₂‐Activation for γ‐Butyrolactones and Its Application in the Total Synthesis of (±)‐Heteroplexisolide E