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Thomas M. Mitzel
Researcher at Ohio State University
Publications - 12
Citations - 345
Thomas M. Mitzel is an academic researcher from Ohio State University. The author has contributed to research in topics: Aqueous solution & Stereoselectivity. The author has an hindex of 6, co-authored 12 publications receiving 340 citations. Previous affiliations of Thomas M. Mitzel include Trinity College (Connecticut) & Keio University.
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Journal ArticleDOI
Addition of Allylindium Reagents to Aldehydes Substituted at Cα or Cβ with Heteroatomic Functional Groups. Analysis of the Modulation in Diastereoselectivity Attainable in Aqueous, Organic, and Mixed Solvent Systems
Leo A. Paquette,Thomas M. Mitzel +1 more
TL;DR: In this paper, the stereochemical course of indium-promoted allylations to α- and β-oxy aldehydes has been investigated in solvents ranging from anhydrous THF to pure H2O.
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Diastereoselection during 1,2-Addition of the Allylindium Reagent to alpha-Thia and alpha-Amino Aldehydes in Aqueous and Organic Solvents.
TL;DR: The stereochemistry of the indium-promoted reaction of allyl bromide with alpha-thia, disubstituted alpha-amino, and protected alpha- amino aldehydes in water has been evaluated, indicating that the allylindium reagent is not thiophilic.
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Chelation control associated with organometallic addition reactions in water. The high stereoselectivity offered by α- and β-hydroxyl substituents obviates the need for protecting groups
Leo A. Paquette,Thomas M. Mitzel +1 more
TL;DR: In this paper, high stereoselectivities have been observed for indium-promoted allylations of α- and β-hydroxy aldehydes in aqueous media, with strong implication that chelate control can continue to operate in water.
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Comparative Diastereoselectivity Analysis of Crotylindium and 3-Bromoallylindium Additions to alpha-Oxy Aldehydes in Aqueous and Nonaqueous Solvent Systems.
Leo A. Paquette,Thomas M. Mitzel +1 more
TL;DR: The couplings of crotyl bromide and 1,3-dibromopropene to a triad of conformationally unrestricted alpha-oxy aldehydes in water, aqueous THF (1:1), and anhydrous THF are described, and a utilitarian example is demonstrated.
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Use of N-Methylformamide as a Solvent in Indium-Promoted Barbier Reactions en Route to Enediyne and Epoxy Diyne Formation: Comparison of Rate and Stereoselectivity in C−C Bond-Forming Reactions with Water
TL;DR: Indium-promoted coupling reactions between propargyl aldehydes and alpha-chloropropargylphenyl sulfide and use of N-methylformamide (NMF) afforded an acceleration of these Barbier-style reactions compared to water, allowing for easy entry into the formation of epoxydiyne and enediyne skeletal structures.