Stereoselective Synthesis of (<i>Z</i>)‐Dihomoallylic Phosphonates with Quaternary Carbon Center by Palladium‐Catalyzed Bisallylation of Vinylethyene Carbonates with <i>β</i>‐Ketophosphonates

Liu, Zhigang; Ke, Miaolin; Zhang, Ke; Zuo, Sheng; Jiang, Meifen; Chen, Fen‐Er

doi:10.1002/ajoc.202100054

Asian J Org Chem

2021

DOI: 10.1002/ajoc.202100054

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Stereoselective Synthesis of (Z)‐Dihomoallylic Phosphonates with Quaternary Carbon Center by Palladium‐Catalyzed Bisallylation of Vinylethyene Carbonates with β‐Ketophosphonates

Zhigang Liu

Miaolin Ke

Ke Zhang

et al.

Abstract: A palladium-catalyzed bisallylation of vinylethylene carbonates with β-ketophosphonates to access to (Z)trisubstituted dihomoallylic phosphonates bearing a quaternary carbon center with good regio-and stereoselectivity is reported. This operationally simple protocol exhibits excellent functional group tolerance to deliver valuable dihomoallylic phosphonates.

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Cited by 11 publications

References 84 publications

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Synergistic Pd/Cu Catalyzed Allylation of Cyclic Ketimine Esters with Vinylethylene Carbonates: Enantioselective Construction of Trisubstituted Allylic 2H‐Pyrrole Derivatives

Zhang

et al. 2022

Adv Synth Catal

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An asymmetric allylation of cyclic ketimine esters with vinylethylene carbonates was accomplished through a Pd/Cu dual catalysis system under a mild condition, providing a range of trisubstituted allylic 2H-pyrrole analogues bearing a chiral quaternary stereogenic center in high yields (up to 92% yield) and with excellent regioselectivities and enantioselectivities (up to 96% ee). A gram-scale operation was also conducted in high efficiency without erosion of enantioselectivity and stereoselectivity.

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Synergistic Pd/Cu Catalyzed Allylation of Cyclic Ketimine Esters with Vinylethylene Carbonates: Enantioselective Construction of Trisubstituted Allylic 2H‐Pyrrole Derivatives

Zhang

et al. 2022

Adv Synth Catal

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Pd‐catalyzed decarboxylative [3 + 2] cycloaddition: Assembly of highly functionalized spirooxindoles bearing two quaternary centers

Zhu

Jiang

et al. 2021

Applied Organom Chemis

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An efficient method for the practical formation of functionalized spirooxindoles, which was accompanied by generating a sterically congested spiroketal system and bearing two quaternary stereocenters via a sequential palladium, catalyzed decarboxylative [3 + 2] cycloaddition of vinylethylene carbonates (VECs) and isatins. Importantly, the redox-neutral catalytic system possesses the characteristics of operational convenience, good functional group tolerance, and good regioselectivity and diastereoselectivity, which enables a diastereoselective synthesis of spiroketal oxindole skeletons in an excellent yield.

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Chemo‐, Regio‐ and Stereoselective Preparation of (Z)‐2‐Butene‐1,4‐Diol Monoesters via Pd‐Catalyzed Decarboxylative Acyloxylation

Cheng,

Zhao,

Zhang

et al. 2024

Chemistry A European J

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(Z)‐alkenes are useful synthons but thermodynamically less stable than their (E)‐isomers and typically more difficult to prepare. The synthesis of 1,4‐hetero‐bifunctionalized (Z)‐alkenes is particularly challenging due to the inherent regio‐ and stereoselectivity issues. Herein we demonstrate a general, chemoselective and direct synthesis of (Z)‐2‐butene‐1,4‐diol monoesters. The protocol operates within a Pd‐catalyzed decarboxylative acyloxylation regime involving vinyl ethylene carbonates (VECs) and various carboxylic acids as the reaction partners under mild and operationally attractive conditions. The newly developed process allows access to a structurally diverse pool of (Z)‐2‐butene‐1,4‐diol monoesters in good yields and with excellent regio‐ and stereoselectivity. Various synthetic transformations of the obtained (Z)‐2‐butene‐1,4‐diol monoesters demonstrate how these synthons are of great use to rapidly diversify the portfolio of these formal desymmetrized (Z)‐alkenes.

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Stereoselective Synthesis of (Z)‐Dihomoallylic Phosphonates with Quaternary Carbon Center by Palladium‐Catalyzed Bisallylation of Vinylethyene Carbonates with β‐Ketophosphonates

Cited by 11 publications

References 84 publications

Synergistic Pd/Cu Catalyzed Allylation of Cyclic Ketimine Esters with Vinylethylene Carbonates: Enantioselective Construction of Trisubstituted Allylic 2H‐Pyrrole Derivatives

Synergistic Pd/Cu Catalyzed Allylation of Cyclic Ketimine Esters with Vinylethylene Carbonates: Enantioselective Construction of Trisubstituted Allylic 2H‐Pyrrole Derivatives

Pd‐catalyzed decarboxylative [3 + 2] cycloaddition: Assembly of highly functionalized spirooxindoles bearing two quaternary centers

Chemo‐, Regio‐ and Stereoselective Preparation of (Z)‐2‐Butene‐1,4‐Diol Monoesters via Pd‐Catalyzed Decarboxylative Acyloxylation

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