ArticleNature communications2023
Asymmetric formal C-C bond insertion into aldehydes via copper-catalyzed diyne cyclization.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
What it found
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Who cites it
6 citing papers in PubMed.
- Copper-catalysed dynamic kinetic (4+1) cyclization of 1,3-enynes for atroposelective arylpyrrole synthesis.Nature communications · 2026Article
- Enantioselective dearomative single-atom skeletal editing of benzofurans.Nature communications · 2025Article
- Copper-catalyzed atroposelective hydroarylation of 1-alkynylindoles.Nature communications · 2025Article
- Ligand-controlled divergent asymmetric C(spNature communications · 2025Article
- Asymmetric Büchner reaction and arene cyclopropanation via copper-catalyzed controllable cyclization of diynes.Nature communications · 2024Article
- Asymmetric one-carbon ring expansion of diverse N-heterocycles via copper-catalyzed diyne cyclization.Science advances · 2024Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
The formal C-C bond insertion into aldehydes is an attractive methodology for the assembly of homologated carbonyl compounds. However, the homologation of aldehydes has been limited to diazo approach and the enantioselective reaction was rarely developed. Herein, we report an asymmetric formal C-C bond insertion into aldehydes through diyne cyclization strategy. In the presence of Cu(I)/SaBOX catalyst, this method leads to the efficient construction of versatile axially chiral naphthylpyrroles in moderate to excellent yields with good to excellent enantioselectivities. This protocol represents a rare example of asymmetric formal C-C bond insertion into aldehydes using non-diazo approach. The combined experimental and computational mechanistic studies reveal the reaction mechanism, origin of regioselectivity and stereoselectivity. Notably, the chiral phosphine ligand derived from synthesized axially chiral skeleton was proven to be applicable to asymmetric catalysis.
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Registered trials
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