ArticleJournal of the American Chemical Society2018
Stereodivergent Rhodium(III)-Catalyzed cis-Cyclopropanation Enabled by Multivariate Optimization.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Modular Assembly of Chiral Cp* Clones Unlocks Performant Catalysts for Enantioselective C-H Functionalizations.Journal of the American Chemical Society · 2026Article
- Unified Synthesis Platform for 1,2,3-Trisubstituted Cyclopentadienyl Ligands Decouples Sterics from Electronics.Journal of the American Chemical Society · 2026Article
- Alkyl sulfonyl fluorides as ambiphiles in the stereoselective palladium(II)-catalysed cyclopropanation of unactivated alkenes.Nature synthesis · 2026Article
- Reductive Cyclopropanation through Bismuth Photocatalysis.Journal of the American Chemical Society · 2024Article
- Article
- Modular Enantioselective Synthesis ofACS catalysis · 2021Article
- Gold-Catalyzed Synthesis of Small Rings.Chemical reviews · 2021Article
- Rh(III)-Catalyzed Cyclopropanation of Unactivated Olefins Initiated by C-H Activation.Synlett : accounts and rapid communications in synthetic organic chemistry · 2019Article
- Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols.Journal of the American Chemical Society · 2019Article
- Chiral cyclopentadienyl RhChemical science · 2019Article
- Mild complexation protocol for chiral CpChemical science · 2019Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
The design of stereodivergent transformations is of great interest to the synthetic community as it allows funneling of a given reaction pathway toward one stereochemical outcome or another by only minor adjustments of the reaction setup. Herein, we present a physical organic approach to invert the sense of induction in diastereoselective cyclopropanation of alkenes with N-enoxyphthalimides through rhodium(III) catalysis. Careful parametrization of catalyst-substrate molecular determinants allowed us to interrogate linear-free energy relationships and establish an intuitive and robust statistical model that correlates an extensive number of data points in high accuracy. Our multivariate correlations-steered mechanistic investigation culminated with a robust and general diastereodivergent cyclopropanation tool where the switch from trans- to cis-diastereoinduction is attributed to a mechanistic dichotomy. Selectivity might be determined by the flexibility of rhodacyclic intermediates derived from ring-opened versus -unopened phthalimides, induced by both their respective ring size and the Sterimol B
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