1453221-33-4

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1453221-32-3 C₁₇H₁₅NO₂ 
• 862906-97-6 tert-butyl 2-oxo-3-phenylindoline-1-carboxylate 
• 107-02-8 acrolein 
• 862907-25-3 1-(tert-butoxycarbonyl)-2-oxo-3-phenylindolin-3-yl tert-butyl carbonate 
• 139018-14-7 3-hydroxy-3-phenyl-1,3-dihydro-indol-2-one 
• 100-58-3 phenylmagnesium bromide 
• 91-56-5 indole-2,3-dione 

Relevant academic research and scientific papers

Nickel(II)-Catalyzed Asymmetric Michael Addition of Oxindoles with Modified N,N,O-Tridentate Chiral Phenanthroline Ligands

Nickel(II)-catalyzed enantioselective Michael addition of N-Boc-oxindole derivatives with methyl vinyl ketone was demonstrated to give the corresponding adducts having chiral all-carbon quaternary centers with up to 87% ee in the presence of axially chira

Enantioselective construction of tetrasubstituted stereogenic carbons through bronsted base catalyzed michael reactions: α′-hydroxy enones as key enoate equivalent

Catalytic and asymmetric Michael reactions constitute very powerful tools for the construction of new C-C bonds in synthesis, but most of the reports claiming high selectivity are limited to some specific combinations of nucleophile/electrophile compound types, and only few successful methods deal with the generation of all-carbon quaternary stereocenters. A contribution to solve this gap is presented here based on chiral bifunctional Bronsted base (BB) catalysis and the use of α′-oxy enones as enabling Michael acceptors with ambivalent H-bond acceptor/donor character, a yet unreported design element for bidentate enoate equivalents. It is found that the Michael addition of a range of enolizable carbonyl compounds that have previously demonstrated challenging (i.e., α-substituted 2-oxindoles, cyanoesters, oxazolones, thiazolones, and azlactones) to α′-oxy enones can afford the corresponding tetrasubstituted carbon stereocenters in high diastereo- and enantioselectivity in the presence of standard BB catalysts. Experiments show that the α′-oxy ketone moiety plays a key role in the above realizations, as parallel reactions under identical conditions but using the parent α,β-unsaturated ketones or esters instead proceed sluggish and/or with poor stereoselectivity. A series of trivial chemical manipulations of the ketol moiety in adducts can produce the corresponding carboxy, aldehyde, and ketone compounds under very mild conditions, giving access to a variety of enantioenriched densely functionalized building blocks containing a fully substituted carbon stereocenter. A computational investigation to rationalize the mode of substrate activation and the reaction stereochemistry is also provided, and the proposed models are compared with related systems in the literature.

Efficient approach for the design of effective chiral quaternary phosphonium salts in asymmetric conjugate additions

An efficient approach for the design of chiral quaternary phosphonium bromides as chiral phase-transfer catalysts was demonstrated. A catalyst library of phosphonium salts with various structures was readily constructed using commercially available chiral phosphines as catalyst precursors, and an optimized catalyst was successfully applied to highly enantioselective conjugate additions under base-free phase-transfer conditions with low catalyst loading.

Amino acid-derived phosphonium salts-catalyzed michael addition of 3-substituted oxindoles

A new type of phosphonium phase-transfer catalyst prepared from easily available chiral amino acids was evaluated in a model reaction between oxindole and methyl vinyl ketone, and the catalyst derived from isoleucine was found to be the best. Michael additions of 3-monosubstituted oxindoles to methyl vinyl ketone, acrolein or propargyl aldehyde proceeded smoothly to afford 3,3-disubstituted oxindoles in good to excellent yields with moderate to excellent ees. Copyright

Palladium-catalyzed asymmetric allylic alkylation of 3-aryloxindoles with allylidene dipivalate: A useful enol pivalate product

Triple A: The catalytic asymmetric allylic alkylation (AAA) of 3-aryloxindoles with allylidene dipivalate is described. This reaction affords stable, synthetically useful enol pivalates in high yield and with excellent regio- and enantioselectivity. A broad range of substrates is tolerated, including unprotected and 3-heteroaryl nucleophiles. Copyright