ArticleJournal of the American Chemical Society2013
Enantioselective functionalization of allylic C-H bonds following a strategy of functionalization and diversification.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Tandem catalytic allylic C-H amination and asymmetric [2,3]-rearrangementChemical science · 2024Article
- General Regio- and Diastereoselective Allylic C-H Oxygenation of Internal Alkenes.Journal of the American Chemical Society · 2024Article
- Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis.Natural products and bioprospecting · 2022Review
- A site-selective amination catalyst discriminates between nearly identical C-H bonds of unsymmetrical disubstituted alkenes.Nature chemistry · 2020Article
- Ir-Catalyzed Intermolecular Branch-Selective Allylic C-H Amidation of Unactivated Terminal Olefins.Journal of the American Chemical Society · 2019Article
- Iron-Catalyzed Direct Olefin Diazidation via Peroxyester Activation Promoted by Nitrogen-Based Ligands.ACS catalysis · 2018Article
- Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Acids through the Umpolung Addition of Trifluoromethyl Imines to Carboxylic Acid Derivatives.Angewandte Chemie (International ed. in English) · 2018Article
- Catalytic allylic oxidation of internal alkenes to a multifunctional chiral building block.Nature · 2017Article
- Oxidation of Hindered Allylic C-H Bonds with Applications to the Functionalization of Complex Molecules.ACS catalysis · 2017Article
- Structurally Diverse Diazafluorene-Ligated Palladium(II) Complexes and Their Implications for Aerobic Oxidation Reactions.Journal of the American Chemical Society · 2016Article
- Diazafluorenone-Promoted Oxidation Catalysis: Insights into the Role of Bidentate Ligands in Pd-Catalyzed Aerobic Aza-Wacker Reactions.ACS catalysis · 2016Article
- Enantioselective construction ofChemical science · 2015Article
- OPolyhedron · 2014Article
- Copper-catalyzed oxidative dehydrogenative carboxylation of unactivated alkanes to allylic esters via alkenes.Journal of the American Chemical Society · 2014Article
- Palladium Catalyzed Aryl C-H Amination with OCatalysis science & technology · 2014Article
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2 authors.
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Abstract
We report the enantioselective functionalization of allylic C-H bonds in terminal alkenes by a strategy involving the installation of a temporary functional group at the terminal carbon atom by C-H bond functionalization, followed by the catalytic diversification of this intermediate with a broad scope of reagents. The method consists of a one-pot sequence of palladium-catalyzed allylic C-H bond oxidation under neutral conditions to form linear allyl benzoates, followed by iridium-catalyzed allylic substitution. This overall transformation forms a variety of chiral products containing a new C-N, C-O, C-S, or C-C bond at the allylic position in good yield with a high branched-to-linear selectivity and excellent enantioselectivity (ee ≤97%). The broad scope of the overall process results from separating the oxidation and functionalization steps; by doing so, the scope of nucleophile encompasses those sensitive to direct oxidative functionalization. The high enantioselectivity of the overall process is achieved by developing an allylic oxidation that occurs without acid to form the linear isomer with high selectivity. These allylic functionalization processes are amenable to an iterative sequence leading to (1,n)-functionalized products with catalyst-controlled diastereo- and enantioselectivity. The utility of the method in the synthesis of biologically active molecules has been demonstrated.
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