Pd-catalyzed oxa-[4 + ] dipolar cycloaddition using 1,4-O/C dipole synthons for the synthesis of O-heterocycles

Transition metal-catalyzed dipolar cycloaddition is one of the most efficient and powerful synthetic strategies to produce diverse heterocycles. In particular, for the construction of oxygen-containing heterocycles, which are valuable structural motifs found in pharmaceuticals and natural compounds,...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-12, Vol.21 (48), p.957-9518
Main Authors: Cho, Ho-Jun, Kim, Ju Hyun
Format: Article
Language:English
Subjects:
Catalysis
Chemical synthesis
Cycloaddition
Dipoles
Oxygen
Palladium
Transition metals
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Summary:Transition metal-catalyzed dipolar cycloaddition is one of the most efficient and powerful synthetic strategies to produce diverse heterocycles. In particular, for the construction of oxygen-containing heterocycles, which are valuable structural motifs found in pharmaceuticals and natural compounds, transition metal-catalyzed oxa-dipolar cycloaddition using an oxygen-containing dipole has emerged as a promising method. In recent years, the 1,4-O/C dipole synthons 2-alkylidenetrimethylene carbonate and 2-hydroxymethylallyl carbonate have been developed and successfully applied to palladium-catalyzed oxa-[4 + n ] dipolar cycloadditions with diverse dipolarophiles. In this review, we summarize recent advances in palladium-catalyzed oxa-[4 + n ] dipolar cycloadditions using 1,4-O/C dipoles including asymmetric catalysis and divergent catalysis toward five- to nine-membered O-heterocycles. This review summarizes Pd-catalyzed oxa-[4 + n ] dipolar cycloadditions of 1,4-O/C dipoles with diverse dipolarophiles, affording five- to nine-membered O-heterocycles.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01619f