One-Pot Nucleophilic Organocatalytic Enantioselective [8 + 2] Cycloadditions of Photogenerated Ketenes with Triflate Tropolones.

Aleksandra Murre, Macarena Eugui, Ana C S Carvalho, Karl Anker Jørgensen, Mikk Kaasik

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Article in Organic letters, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 · Who and what money

Authors and funding

5 authors.

Aleksandra MurreDepartment of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia.

Macarena EuguiDepartment of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark.

Ana C S CarvalhoDepartment of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia.

Karl Anker JørgensenDepartment of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark.ORCID 0000-0002-3482-6236

Mikk KaasikDepartment of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia.ORCID 0000-0003-1141-3604

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

This work presents diazoketones as ketene precursors under photochemical conditions, in conjunction with an isothiourea catalyst, to enable an enantioselective [8 + 2] cycloaddition with triflate-substituted tropolones affording 7,5-fused lactone scaffolds. The cycloadducts are obtained in up to 99% yield with up to excellent diastereoselectivity (>20:1 d.r.) and enantioselectivity (up to 99% ee). Furthermore, it is demonstrated that the 7,5-fused lactone can undergo diverse attractive transformations.

Identifiers

PMID42207925

DOI10.1021/acs.orglett.6c01642

PMCPMC13270640

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