Synthesis of Chromone‐Spiroindolinone‐Cyclopentene Derivatives through Phosphine‐Catalyzed (3+2) Annulation of Morita‐Baylis‐Hillman Carbonates with Oxindole‐Chromones

Wang, Bo; Hu, Yimin; Guo, Hongchao; Lei, Tao

doi:10.1002/slct.202203340

Cited by 4 publications

(2 citation statements)

References 66 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Chiral phosphines are often employed as the catalysts in various asymmetric annulation reactions of Morita–Baylis–Hillman (MBH) carbonates or acetates with unsaturated substrates . P-Stereogenic phosphines also serve as efficient catalysts in this kind of reaction, as shown in Schemes –. ,− …”

Section: Applications Of P-stereogenic Phosphorus Ligands In Asymmetr...mentioning

confidence: 99%

P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis

Imamoto

2024

Chem. Rev.

View full text Add to dashboard Cite

Chiral phosphorus ligands play a crucial role in asymmetric catalysis for the efficient synthesis of useful optically active compounds. They are largely categorized into two classes: backbone chirality ligands and P-stereogenic phosphorus ligands. Most of the reported ligands belong to the former class. Privileged ones such as BINAP and DuPhos are frequently employed in a wide range of catalytic asymmetric transformations. In contrast, the latter class of P-stereogenic phosphorus ligands has remained a small family for many years mainly because of their synthetic difficulty. The late 1990s saw the emergence of novel P-stereogenic phosphorus ligands with their superior enantioinduction ability in Rh-catalyzed asymmetric hydrogenation reactions. Since then, numerous P-stereogenic phosphorus ligands have been synthesized and used in catalytic asymmetric reactions. This Review summarizes P-stereogenic phosphorus ligands reported thus far, including their stereochemical and electronic properties that afford high to excellent enantioselectivities. Examples of reactions that use this class of ligands are described together with their applications in the construction of key intermediates for the synthesis of optically active natural products and therapeutic agents. The literature covered dates back to 1968 up until December 2023, centering on studies published in the late 1990s and later years.

show abstract

Section: Applications Of P-stereogenic Phosphorus Ligands In Asymmetr...mentioning

confidence: 99%

P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis

Imamoto

2024

Chem. Rev.

View full text Add to dashboard Cite

show abstract

“…2 Therefore, exploring novel approaches for the construction of diverse chromone derivatives has been the focus of intensive efforts, and numerous significant advances have been made in the field of catalysis. 3 Transition metal-catalyzed domino reaction has been proven as an effective approach to assemble complex molecules by forging two or more new chemical bonds from readily available substrates in one single operation. 4 In this context, the Catellani-type annulation cooperatively catalyzed by palladium and norbornene (NBE) represents a powerful tool for the construction of complex arenes.…”

Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed decarboxylation [2 + 2 + 2] annulation approach to chromone-containing polycyclic compounds

et al. 2023

View full text Add to dashboard Cite

show abstract

Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles

Li,

Ma,

Meng

et al. 2023

Adv Synth Catal

View full text Add to dashboard Cite

Spirooxindoles are privileged scaffolds in diverse bioactive natural products and pharmaceuticals, significant achievements for the construction of these molecules have thus been made in the past years. Among them, organocatalysis, in particular, nucleophilic Lewis base catalysis, has recently emerged as an efficient and reliable method for the preparation of diverse and valuable functionalized spirooxindoles. According to different kinds of nucleophilic catalysts, we summarize and classify three catalytic strategies; these are tertiary amine‐catalyzed cycloadditions, NHC‐catalyzed cycloadditions, and tertiary phosphine‐catalyzed cycloadditions, respectively. Through these methods, potential bioactive spirooxindole skeletons owning various functional groups can be produced to enrich the small organic molecule library. In this review, we describe a comprehensive and updated advances of nucleophilic Lewis base catalytic cycloaddition reactions for the construction of spirooxindoles. Meanwhile, the related mechanism and the application of these annulation strategies in natural product total synthesis will be highlighted in detail.

show abstract

Synthesis of Chromone‐Spiroindolinone‐Cyclopentene Derivatives through Phosphine‐Catalyzed (3+2) Annulation of Morita‐Baylis‐Hillman Carbonates with Oxindole‐Chromones

Cited by 4 publications

References 66 publications

P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis

P-Stereogenic Phosphorus Ligands in Asymmetric Catalysis

Palladium-catalyzed decarboxylation [2 + 2 + 2] annulation approach to chromone-containing polycyclic compounds

Recent Advances in Nucleophilic Lewis Base‐Catalyzed Cycloadditions for Synthesis of Spirooxindoles

Contact Info

Product

Resources

About