1440935-70-5

Upstream product

• 108-05-4 vinyl acetate 
• 92552-73-3 1-benzyl-3-hydroxyindolin-2-one 
• 1217-89-6 1-benzylisatin 
• 74-86-2 acetylene 
• 100-39-0 benzyl bromide 
• 91-56-5 indole-2,3-dione 

Downstream Products

• 1440934-42-8 (S)-1-benzyl-3-hydroxy-3-vinylindolin-2-one 
• 1449291-30-8 C₂₆H₂₁NO₃ 

Relevant academic research and scientific papers

Ruthenium(0)-Catalyzed C-C Coupling of Alkynes and 3-Hydroxy-2-oxindoles: Direct C-H Vinylation of Alcohols

Upon exposure to a ruthenium(0) catalyst, N-benzyl-3-hydroxy-2-oxindoles react with diverse alkynes to form products of C-H vinylation with complete control of regioselectivity and olefin geometry. This method contributes to a growing body of catalytic processes that enable direct conversion of lower alcohols to higher alcohols in the absence of stoichiometric organometallic reagents.

A C=O???Isothiouronium Interaction Dictates Enantiodiscrimination in Acylative Kinetic Resolutions of Tertiary Heterocyclic Alcohols

A combination of experimental and computational studies have identified a C=O???isothiouronium interaction as key to efficient enantiodiscrimination in the kinetic resolution of tertiary heterocyclic alcohols bearing up to three potential recognition motifs at the stereogenic tertiary carbinol center. This discrimination was exploited in the isothiourea-catalyzed acylative kinetic resolution of tertiary heterocyclic alcohols (38 examples, s factors up to >200). The reaction proceeds at low catalyst loadings (generally 1 mol %) with either isobutyric or acetic anhydride as the acylating agent under mild conditions.

Diversity-Oriented Synthesis of Oxacyclic Spirooxindole Derivatives through Ring-Closing Enyne Metathesis and Intramolecular Pauson–Khand (2+2+1) Cyclization of Oxindole Enynes

An efficient approach for a reagent-based diversity-oriented synthesis (DOS) of novel fused spirooxindole scaffolds from oxindole enynes has been developed. The reaction involves a metal-catalyzed C-3 allylation/vinylation/homoallylation of N-substituted isatins which gives rise to the corresponding alcohols that can be converted into the required enynes. Further transformation to diverse complex molecular scaffolds proceeds via a subsequent ruthenium-catalyzed ring-closing enyne metathesis (RCEYM), or cobalt-catalyzed intramolecular Pauson–Khand (2+2+1) cyclization reaction (IPKR). This strategy provides a facile approach to various spirooxindole-vinyldihydropyrans/tetrahydrooxepines and spirocyclic fused cyclopentenones in good to excellent yields. (Figure presented.).

A Metallacycle Fragmentation Strategy for Vinyl Transfer from Enol Carboxylates to Secondary Alcohol C-H Bonds via Osmium- or Ruthenium-Catalyzed Transfer Hydrogenation

A strategy for catalytic vinyl transfer from enol carboxylates to activated secondary alcohol C-H bonds is described. Using XPhos-modified ruthenium(0) or osmium(0) complexes, enol carboxylate-carbonyl oxidative coupling forms transient β-acyloxy-oxametallacycles, which eliminate carboxylate to deliver allylic ruthenium(II) or osmium(II) alkoxides. Reduction of the metal(II) salt via hydrogen transfer from the secondary alcohol reactant releases the product of carbinol C-H vinylation and regenerates ketone and zero-valent catalyst.

Kinetic resolution of tertiary alcohols: Highly enantioselective access to 3-hydroxy-3-substituted oxindoles

Enantioselective: The first highly enantioselective kinetic resolution of 3-hydroxy-3-substituted oxindoles has been developed through oxidative esterification catalyzed by a N-heterocyclic carbene (see picture). This method uses a simple procedure and provides 3-hydroxy-oxindoles with various substituents at the 3-position in excellent enantiopurity. S=selectivity. Copyright