What question did this study set out to answer?

The aim is to explore the synthesis of spiro-BCH derivatives through a palladium-catalyzed reaction.

May 9, 2026Organic Letters0 citations

Palladium-Catalyzed Sequential Intramolecular Annulation/2σ + 2π Cycloaddition of 5-Allenyloxazolidine-2,4-Diones and Bicyclobutanes

YDYujie DongInstitute of Food Science & Technology NZNianci ZhangChina Agricultural University CWC Y WangChinese Center For Disease Control and Prevention

Key Points

The aim is to explore the synthesis of spiro-BCH derivatives through a palladium-catalyzed reaction.
Palladium-catalyzed tandem intramolecular annulation and [2σ + 2π] cycloaddition
Utilized 5-allenyloxazolidine-2,4-diones and bicyclo[1.1.0]butanes
Evaluated substrate scope and derivatization
Achieved moderate to excellent yields of γ-lactam-spiro-BCH scaffolds
Demonstrated broad substrate scope for different derivatives
Showcased good scalability and versatility for downstream derivatization

Abstract

Bicyclo2.1.1hexanes (BCHs) are important three-dimensional bioisosteres of substituted benzenes. Although mono- and fused-BCH scaffolds have been extensively studied, spiro-BCH derivatives remain relatively underexplored. Herein, we report a palladium-catalyzed tandem intramolecular annulation/strain-release 2σ + 2π cycloaddition between 5-allenyloxazolidine-2,4-diones and bicyclo1.1.0butanes (BCBs). This method provides efficient and concise access to a novel class of γ-lactam-spiro-BCH scaffolds in moderate to excellent yields. The transformation exhibits broad substrate scope, good scalability, and versatile downstream derivatization of the products.

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