Palladium-catalysed enantio- and regioselective (3 + 2) cycloaddition reactions of sulfamidate imine-derived 1-azadienes towards spirocyclic cyclopentanes

Pham, Quoc Hoang; Tague, Andrew J.; Richardson, Christopher; Gardiner, Michael G.; Pyne, Stephen G.; Hyland, Christopher J. T.

doi:10.1039/d3sc01510f

Cited by 8 publications

(1 citation statement)

References 64 publications

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“…The method was subsequently extended to vinyl cyclopropanes, resulting in the The same group recently explored the Pd-catalysed formal (3+2) cycloaddition of sulfamidate imine azadienes. 113 This involved the use of the azadienes as the electrophile and the disubstituted vinylcypropanes as the nucleophile. The authors initiated their exploration by conducting a comprehensive assessment of various ligand classes, as illustrated in Scheme 95.…”

Section: Oxazolidin-4-onesmentioning

confidence: 99%

Pd-Catalysed asymmetric allylic alkylation of heterocycles: a user's guide

Richard,

Clark,

Hannam

et al. 2024

Chem. Soc. Rev.

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Section: Oxazolidin-4-onesmentioning

confidence: 99%

Pd-Catalysed asymmetric allylic alkylation of heterocycles: a user's guide

Richard,

Clark,

Hannam

et al. 2024

Chem. Soc. Rev.

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Synthesis of Bridged Bicyclic Systems peri‐Annulated to the Indole Ring: Tropane‐Fused Indoles

Antropov,

Tokmacheva,

Levina

et al. 2024

Adv Synth Catal

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Ytterbium(III) triflate catalysed domino reaction of (3‐formyl‐4‐indolyl)‐derived donor‐acceptor cyclopropane with primary amines provides a simple approach to an unprecedented tetracyclic skeleton in which tropane system is peri‐annulated with an indole core. This process involves the formation of an imine and its (3+2)‐cross‐cycloaddition with donor‐acceptor cyclopropane moiety, yielding indole core under mild reaction conditions. These products are of significant interest for pharmacology as potential hybrid molecules with a dual mode of action.tropane‐fused

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Catalytic Asymmetric Cycloadditions of Cyclic Sulfamidate Imines: Straightforward Access to Chiral N‐Heterocycles

Park,

Hyun Kim

2024

Adv Synth Catal

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Chiral N‐heterocyclic compounds are key structures in natural compounds and pharmaceuticals, and they serve as essential building blocks of functional materials. Catalytic asymmetric cycloaddition reactions represent one of the most efficient synthetic strategies for constructing optically active heterocycles. Cyclic sulfamidate imines have recently come to be extensively studied and widely utilized in both organocatalytic and transition metal‐catalyzed asymmetric cycloadditions, where they have been shown to provide various N‐fused‐heterocycles and spiro‐cycles exhibiting high efficiencies with excellent stereoselectivities. This review highlights recent advancements in catalytic asymmetric cycloadditions of cyclic sulfamidate imines for the stereoselective synthesis of biologically active sulfamidate‐containing heterocycles since 2012 while focusing on the diverse reactivities of cyclic sulfamidate imines and the mechanisms of chiral induction in catalysis.

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Palladium-catalysed enantio- and regioselective (3 + 2) cycloaddition reactions of sulfamidate imine-derived 1-azadienes towards spirocyclic cyclopentanes

Abstract: Formation of valuable spiroheterocycles with multiple contiguous stereogenic centres from palladium-catalysed enantioselective (3 + 2) cycloaddition reactions of sulfamidate-derived azadienes and vinylcyclopropanes.

Cited by 8 publications

References 64 publications

Pd-Catalysed asymmetric allylic alkylation of heterocycles: a user's guide

Pd-Catalysed asymmetric allylic alkylation of heterocycles: a user's guide

Synthesis of Bridged Bicyclic Systems peri‐Annulated to the Indole Ring: Tropane‐Fused Indoles

Catalytic Asymmetric Cycloadditions of Cyclic Sulfamidate Imines: Straightforward Access to Chiral N‐Heterocycles

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