ArticleJournal of the American Chemical Society2014
Cation control of diastereoselectivity in iridium-catalyzed allylic substitutions. Formation of enantioenriched tertiary alcohols and thioethers by allylation of 5H-oxazol-4-ones and 5H-thiazol-4-ones.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Article
- Experimental and Computational Studies on Cobalt(I)-Catalyzed Regioselective Allylic Alkylation Reactions.Angewandte Chemie (International ed. in English) · 2023Article
- Rhodium-Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans.Angewandte Chemie (International ed. in English) · 2020Article
- Transition metal catalyzed stereodivergent synthesis ofChemical science · 2019Article
- Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation.Angewandte Chemie (International ed. in English) · 2018Article
- Direct Asymmetric Alkylation of Ketones: Still Unconquered.Angewandte Chemie (International ed. in English) · 2017Review
- Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates.Angewandte Chemie (International ed. in English) · 2017Article
- Stereodivergent Allylic Substitutions with Aryl Acetic Acid Esters by Synergistic Iridium and Lewis Base Catalysis.Journal of the American Chemical Society · 2017Article
- Iridium-Catalyzed Stereoselective Allylic Alkylation Reactions with Crotyl Chloride.Angewandte Chemie (International ed. in English) · 2016Article
- Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles.Angewandte Chemie (International ed. in English) · 2016Article
- Iridium-Catalyzed Diastereo-, Enantio-, and Regioselective Allylic Alkylation with Prochiral Enolates.ACS catalysis · 2016Article
- Asymmetric [4 + 2] annulation of 5Chemical science · 2016Article
- Iridium-Catalyzed Diastereoselective and Enantioselective Allylic Substitutions with Acyclic α-Alkoxy Ketones.Angewandte Chemie (International ed. in English) · 2016Article
- Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5Beilstein journal of organic chemistry · 2016Article
- 1H-Imidazol-4(5H)-ones and thiazol-4(5H)-ones as emerging pronucleophiles in asymmetric catalysis.Beilstein journal of organic chemistry · 2016Review
- Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides.Journal of the American Chemical Society · 2015Article
- Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles.Chemical science · 2015Article
- Highly enantioselective construction of tertiary thioethers and alcoholsChemical science · 2015Article
- Diastereo- and enantioselective iridium-catalyzed allylation of cyclic ketone enolates: synergetic effect of ligands and barium enolates.Journal of the American Chemical Society · 2014Article
- Iridium-catalyzed regio- and enantioselective allylic substitution of silyl dienolates derived from dioxinones.Angewandte Chemie (International ed. in English) · 2014Article
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Abstract
We report highly diastereo- and enantioselective allylations of substituted 5H-oxazol-4-ones and 5H-thiazol-4-ones catalyzed by a metallacyclic iridium complex. Enantioselective Ir-catalyzed allylation of substituted 5H-oxazol-4-ones occurs with high diastereoselectivity by employing the corresponding zinc enolates; enantioselective Ir-catalyzed allylation of substituted 5H-thiazol-4-ones occurs with the corresponding magnesium enolates with high diastereoselectivity. The allylation of substituted 5H-oxazol-4-ones provides rapid access to enantioenriched tertiary α-hydroxy acid derivatives unavailable through Mo-catalyzed allylic substitution. The allylation of substituted 5H-thiazol-4-ones provides a novel method to synthesize enantioenriched tertiary thiols and thioethers. The observed cation effect implies a novel method to control the diastereoselectivity in Ir-catalyzed allylic substitution.
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