Catalytic and Enantioselective Synthesis of Inherently Chiral Saddle-Shaped Compounds by [2 + 2 + 2] Cycloaddition of 1,8-Naphthylene-Based 1,10-Diynes with Alkynoates.

Takanori Shibata, Masahiro Nakada, Kousuke Senda, Mamoru Ito

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Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. 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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4 authors.

Takanori ShibataDepartment of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo, 169-8555, Japan.ORCID https://orcid.org/0000-0003-4436-8264

Masahiro NakadaDepartment of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo, 169-8555, Japan.

Kousuke SendaDepartment of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo, 169-8555, Japan.

Mamoru ItoDepartment of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo, 169-8555, Japan.

Funding

JSPS KAKENHI 23K17922Waseda University 2024C-161

6 · The paper itself

Abstract

In this paper, we describe a chiral Rh-catalyzed [2 + 2 + 2] cycloaddition of 1,8-naphthylene-based 1,10-diynes of an anti/syn mixture with alkynoates. Thermodynamically stable saddle-shaped chiral cycloadducts were obtained in good-to-high yields and enantiomeric ratios. Hetero [2 + 2 + 2] cycloaddition using aryl cyanides also proceeded to give the corresponding inherently chiral pyridine-containing compounds.

Indexed as

cycloadditioninherent chiralityrh catalystsaddle‐shape

Identifiers

PMID40289681

DOI10.1002/chem.202501193

PMCPMC12144861

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