ArticleChemical science2019
Gold(i)-catalyzed stereoselective cyclization of 1,3-enyne aldehydes by a 1,3-acyloxy migration/Nazarov cyclization/aldol addition cascade.
Article in Chemical science, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Taming the reactive intermediates: the nazarov cyclization as a programmable platform.Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents · 2026Review
- Central-to-Axial-to-Central Chirality Transfer in the Au(I)-Catalyzed Cycloisomerization of Propargyl Vinyl Ethers to Cyclopentadienes.The Journal of organic chemistry · 2025Article
- Total synthesis and target identification of marine cyclopiane diterpenes.Nature communications · 2024Article
- Synthesis of 1,3-Enynes by Iron-Catalyzed Propargylic C-H Functionalization: An Alkyne Analogue for the Eschenmoser Methenylation.Organic letters · 2024Article
- Synthesis of 5-Hydrazino-2-cyclopentenone Derivatives by a Gold(I)-Catalyzed Cycloisomerization/Hetero-Diels-Alder/Ring-Opening Tandem Reaction of Enynyl Acetates.The Journal of organic chemistry · 2023Article
- Bifunctional Phosphine-Enabled Regioselective Cycloisomerization of Enynyl Esters En Route to Bicyclo[2.2.1]heptenes.Organic letters · 2023Article
- C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by tuning Pd catalytic modes: Pd(i)-Pd(ii) catalysisChemical science · 2021Article
- Gold-Catalyzed Synthesis of Chiral Cyclopentadienyl Esters via Chirality Transfer.Organic letters · 2020Article
- Facile access to diverse all-carbon quaternary center containing spirobicycles by exploring a tandem Castro-Stephens coupling/acyloxy shift/cyclization/semipinacol rearrangement sequence.Chemical science · 2020Article
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Authors and funding
3 authors.
Funding
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Abstract
Stereoselective synthesis of bicyclo[3.3.0]octenones from chiral 1,3-enyne aldehydes bearing propargylic acetates is described. The method is based on a Au(i)-catalyzed domino sequence with concomitant transfer of chirality involving 1,3-acyloxy migration followed by Nazarov cyclization and an unprecedented aldol addition. The method furnishes densely functionalized bicyclic structures in high yields, with up to 97% ee and good diastereoselectivity.
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