ArticleJournal of the American Chemical Society2013
Mechanistic basis for high stereoselectivity and broad substrate scope in the (salen)Co(III)-catalyzed hydrolytic kinetic resolution.
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 16 papers.
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16 citing papers in PubMed.
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- Parallel kinetic resolution of aziridinesChemical science · 2023Article
- Multimetallic-Catalyzed C-C Bond-Forming Reactions: From Serendipity to Strategy.Journal of the American Chemical Society · 2023Review
- Chloride-Mediated Alkene Activation Drives Enantioselective Thiourea and Hydrogen Chloride Co-Catalyzed Prins Cyclizations.Journal of the American Chemical Society · 2022Article
- Dynamic kinetic resolution of transient hemiketals: a strategy for the desymmetrisation of prochiral oxetanols.Chemical science · 2022Article
- A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Brønsted- and Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings.Journal of the American Chemical Society · 2021Article
- Mechanistic Studies Inform Design of Improved Ti(salen) Catalysts for Enantioselective [3 + 2] Cycloaddition.Journal of the American Chemical Society · 2020Article
- Mechanistic Study of Isotactic Poly(propylene oxide) Synthesis using a Tethered Bimetallic Chromium Salen Catalyst.ACS catalysis · 2020Article
- Al(Salen) Metal Complexes in Stereoselective Catalysis.Molecules (Basel, Switzerland) · 2019Review
- The In Situ Enzymatic Screening (ISES) Approach to Reaction Discovery and Catalyst Identification.Current protocols in chemical biology · 2017Article
- A Simple Graphical Method to Determine the Order in Catalyst.Angewandte Chemie (International ed. in English) · 2016Article
- Crystal structure of an unknown solvate of {2,2'-[ethane-1,2-diylbis(nitrilo-methanylyl-idene)]diphenolato-κ(4) O,N,N',O'}(N-ferrocenylisonicotinamide-κN (1))cobalt(II): a Co(II)-salen complex that forms hydrogen-bonded dimers.Acta crystallographica. Section E, Crystallographic communications · 2015Article
- Mini-ISES identifies promising carbafructopyranose-based salens for asymmetric catalysis: Tuning ligand shape via the anomeric effect.Science advances · 2015Article
- Simple, chemoselective, catalytic olefin isomerization.Journal of the American Chemical Society · 2014Article
- A broadly applicable and practical oligomeric (salen) Co catalyst for enantioselective epoxide ring-opening reactions.Tetrahedron · 2014Article
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Abstract
In the (salen)Co(III)-catalyzed hydrolytic kinetic resolution (HKR) of terminal epoxides, the rate- and stereoselectivity-determining epoxide ring-opening step occurs by a cooperative bimetallic mechanism with one Co(III) complex acting as a Lewis acid and another serving to deliver the hydroxide nucleophile. In this paper, we analyze the basis for the extraordinarily high stereoselectivity and broad substrate scope observed in the HKR. We demonstrate that the stereochemistry of each of the two (salen)Co(III) complexes in the rate-determining transition structure is important for productive catalysis: a measurable rate of hydrolysis occurs only if the absolute stereochemistry of each of these (salen)Co(III) complexes is the same. Experimental and computational studies provide strong evidence that stereochemical communication in the HKR is mediated by the stepped conformation of the salen ligand, and not the shape of the chiral diamine backbone of the ligand. A detailed computational analysis reveals that the epoxide binds the Lewis acidic Co(III) complex in a well-defined geometry imposed by stereoelectronic rather than steric effects. This insight serves as the basis of a complete stereochemical and transition structure model that sheds light on the reasons for the broad substrate generality of the HKR.
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