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.
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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.
108
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TL;DR: The enantioselective synthesis of the eunicellin ophirin B has been completed with a ring-closing metathesis providing efficient access to the oxonene ring and a highly diastereoselectively intramolecular Diels-Alder reaction results in the formation of the hydrobenzofuran portion of the molecule.
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1.1 – Allyl Organometallics
William R. Roush
- 01 Jan 1991
TL;DR: In this paper, the development of highly stereoselective syntheses of the so-called propionate segments that are commonly found in acyclic molecules has been studied.
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