ArticleNature communications2014
Highly stereoselective synthesis of cyclopentanes bearing four stereocentres by a rhodium carbene-initiated domino sequence.
Article in Nature communications, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Cascade MHAT Radical Cyclopentannulation of Skipped Enyne to Access Highly Functionalized Carbocycles.JACS Au · 2026Article
- Pyridoxal 5'-Phosphate-Dependent Enzymatic Decarboxylative Annulation.Journal of the American Chemical Society · 2026Article
- Asymmetric C-H Functionalization ofJournal of the American Chemical Society · 2025Article
- In Silico Approach to Design of New Multi-Targeted Inhibitors Based on Quinoline Ring with Potential Anticancer Properties.International journal of molecular sciences · 2025Article
- Recent advances in metal-catalysed asymmetric sigmatropic rearrangements.Chemical science · 2022Review
- Polyhydroxylated Cyclopentane β-Amino Acids Derived from d-Mannose and d-Galactose: Synthesis and Protocol for Incorporation into Peptides.ACS omega · 2022Article
- Scope and mechanistic investigations of Pd-catalyzed coupling/cyclizations and cycloisomerizations of allenyl malonates.ACS catalysis · 2021Article
- Gold(I)-catalyzed intramolecular cyclization/intermolecular cycloaddition cascade as a fast track to polycarbocycles and mechanistic insights.Nature communications · 2021Article
- Recent Perspectives on Rearrangement Reactions of Ylides via Carbene Transfer Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Regio- and Diastereoselective Dimerization of Diazo Carbonyls: A Cooperative Catalytic Approach to Complex Scaffolds with Four Contiguous Stereocenters.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides.Nature chemistry · 2017Article
- Asymmetric synthesis of cyclopentanes bearing four contiguous stereocenters via an NHC-catalyzed Michael/Michael/esterification domino reaction.Chemical communications (Cambridge, England) · 2016Article
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Abstract
Stereoselective synthesis of a cyclopentane nucleus by convergent annulation constitutes a significant challenge for synthetic chemists. Although a number of biologically relevant cyclopentane natural products are known, more often than not, the cyclopentane core is assembled in a stepwise manner because of the lack of efficient annulation strategies. Here we report the rhodium-catalysed reactions of vinyldiazoacetates with (E)-1,3-disubstituted 2-butenols generate cyclopentanes, containing four new stereogenic centres with very high levels of stereoselectivity (99% ee, >97: 3 dr). The reaction proceeds by a carbene-initiated domino sequence consisting of five distinct steps: rhodium-bound oxonium ylide formation, [2,3]-sigmatropic rearrangement, oxy-Cope rearrangement, enol-keto tautomerization and finally an intramolecular carbonyl ene reaction. A systematic study is presented detailing how to control chirality transfer in each of the four stereo-defining steps of the cascade, consummating in the development of a highly stereoselective process.
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