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

Literature Information

Publication Date 2023-11-20
DOI 10.1039/D3OB01619F
Impact Factor 3.876
Authors

Ho-Jun Cho, Ju Hyun Kim


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Abstract

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.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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