Highly Functional Allyl-Bicyclo[1.1.1]pentane Synthesis by Radical-Initiated Three-Component Stereoselective Allylation DOI Creative Commons
Qian Zeng,

Wangyu Shi,

Arjan W. Kleij

и другие.

JACS Au, Год журнала: 2025, Номер 5(2), С. 913 - 921

Опубликована: Фев. 11, 2025

Rapid access to highly functional allylated BCP synthons can be achieved with good selectivity and yield through a radical, three-component reaction (3CR) regime using various combinations of radical precursors vinyl-appended heterocycles acting as versatile modular precursors. This practical process combines mild operating conditions, wide scope partners, the ability diversify functionalized allylic scaffolds further allyl other groups synthetic branching points. The developed protocol allows structural alteration increases molecular complexity late-stage drug modifications conjugation approaches. Mechanistic probes demonstrate that 3CR is initiated by selective, light-promoted addition [1.1.1]-propellane, followed coupling vinyl-substituted heterocycle, which represents formal decarboxylative addition/double bond relay/protonation sequence.

Язык: Английский

Highly Functional Allyl-Bicyclo[1.1.1]pentane Synthesis by Radical-Initiated Three-Component Stereoselective Allylation DOI Creative Commons
Qian Zeng,

Wangyu Shi,

Arjan W. Kleij

и другие.

JACS Au, Год журнала: 2025, Номер 5(2), С. 913 - 921

Опубликована: Фев. 11, 2025

Rapid access to highly functional allylated BCP synthons can be achieved with good selectivity and yield through a radical, three-component reaction (3CR) regime using various combinations of radical precursors vinyl-appended heterocycles acting as versatile modular precursors. This practical process combines mild operating conditions, wide scope partners, the ability diversify functionalized allylic scaffolds further allyl other groups synthetic branching points. The developed protocol allows structural alteration increases molecular complexity late-stage drug modifications conjugation approaches. Mechanistic probes demonstrate that 3CR is initiated by selective, light-promoted addition [1.1.1]-propellane, followed coupling vinyl-substituted heterocycle, which represents formal decarboxylative addition/double bond relay/protonation sequence.

Язык: Английский

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