Journal Article10.1002/HC.20331
Development of new methods for asymmetric synthesis based on sulfoximines
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TL;DR: Sulfoximine-substituted bis(allyl)titanium complexes, which are configurationally labile at the Cα-atoms, have emerged as valuable reagents in asymmetric synthesis as discussed by the authors.
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Abstract: Sulfoximine-substituted bis(allyl)titanium complexes, which are configurationally labile at the Cα-atoms, have emerged as valuable reagents in asymmetric synthesis. Their highly selective reactions with aldehydes and N-sulfonyl imino esters allow the attainment of enantio- and diastereomerically pure sulfoximine-substituted homoallylic alcohols and homoallylic amines, respectively, which are valuable starting materials for the asymmetric synthesis of homopropargylic alcohols, 2,3-dihydrofurans, medium-sized carbocycles and lactones, unsaturated mono- and bicyclic prolines, β-amino acids, and vinyl oxiranes, respectively. The high synthetic versatility of the sulfoximine group stems from its ability to function as a chiral carbanion-stabilizing nucleofuge. © 2007 Wiley Periodicals, Inc. 18:472–481, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20331
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Citations
Sulfoximines from a Medicinal Chemist's Perspective: Physicochemical and in vitro Parameters Relevant for Drug Discovery.
TL;DR: It is demonstrated that the sulfoximine moiety is a chemically stable, comparatively polar and weakly basic functional group, often leading to favorable aqueous solubility, permeability and metabolic stability.
373
Light‐Induced Ruthenium‐Catalyzed Nitrene Transfer Reactions: A Photochemical Approach towards N‐Acyl Sulfimides and Sulfoximines
TL;DR: A light-induced ruthenium-catalyzed N-acyl nitrene transfer to sulfides and sulfoxides by decarboxylation of 1,4,2-dioxazol-5-ones at room temperature, thus providing direct access to N-ACYl sulfimides and sulphoximines under mild reaction conditions.
225
Fluorinated sulfoximines: syntheses, properties and applications.
TL;DR: The exceptional electronic effects induced by the presence of strongly electron-withdrawing fluoro-bearing sulfonimidoyl moieties allowed the development of remarkable super-acidifiers and super-acceptors with relevance in materials sciences.
209
Organocatalytic Kinetic Resolution of Sulfoximines
TL;DR: An efficient kinetic resolution of sulfoximines with enals was realized using chiral N-heterocyclic carbene (NHC) catalysts and the stereoselective amidation proceeds without additional acyl transfer agent.
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Iron-Catalyzed Hetero-Cross-Dehydrogenative Coupling Reactions of Sulfoximines with Diarylmethanes: A New Route to N-Alkylated Sulfoximines
TL;DR: An efficient iron-catalyzed C-N bond formation by hetero-cross-dehydrogenative coupling (CDC) between sulfoximines and diarylmethanes is described and provides N-alkylated sulf oximines in moderate to good yields.
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References
Asymmetric Synthesis of 2,3-Dihydrofurans by Reaction of Rhodium-Stabilized Vinylcarbenoids with Vinyl Ethers.
Huw M. L. Davies,Gulzar Ahmed,Rebecca L. Calvo,Melvyn Rowen Churchill,David George Churchill +4 more
TL;DR: Rhodium(II) octanoate catalyzed decomposition of 2-diazo-3-siloxybutenoates, containing (R)-pantolactone as a chiral auxiliary, in the presence of vinyl ethers results in the diastereoselective synthesis of cyclopropanes with high asymmetric induction.
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Preparation of Chiral Allenylmetal Reagents from Enantioenriched Allenyl Iodides and Propargylic Mesylates. A Comparison of Indium, Bismuth, and Tin Derivatives.
TL;DR: From experiments, it was determined that allenylindium bromides and allenyltin bromide are configurationally stable under the reaction conditions.
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Asymmetric Synthesis of Unsaturated, Fused Bicyclic Proline Analogues through Amino Alkylation of Cyclic Bis(allylsulfoximine)titanium Complexes and Migratory Cyclization of δ-Amino Alkenyl Aminosulfoxonium Salts
TL;DR: An asymmetric synthesis of new Delta(3a,4)-unsaturated, fused bicyclic proline analogues from cyclic bis(allylsulfoximine)titanium complexes and N-tert-butylsulfonyl imino ethyl ester is described.
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