21034-21-9

Upstream product

• 75-21-8 oxirane 
• 64-17-5 ethanol 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 96-48-0 4-butanolide 
• 93-89-0 benzoic acid ethyl ester 
• 31167-92-7 α-iodo-γ-butyrolactone 
• 98-88-4 benzoyl chloride 
• 109-99-9 tetrahydrofuran 
• 100-52-7 benzaldehyde 
• 1373611-11-0 1-benzoylcyclopropane-1-carboxamide 
• 497-23-4 2-buten-4-olide 
• 161144-22-5 2-Benzoyl-4,5-dihydrofuran 
• 1523-12-2 2-nitrophenyl benzoate 
• 93-58-3 benzoic acid methyl ester 

Downstream Products

• 39755-06-1 4-Oxo-4-phenyl-1-acetoxybutane 
• 21574-62-9 2-amino-5-(2-hydroxy-ethyl)-6-phenyl-3H-pyrimidin-4-one 
• 21574-62-9 2-amino-5-(2-hydroxy-ethyl)-6-phenyl-3H-pyrimidin-4-one 
• 80857-06-3 2-benzoil-2-clorobutirrolattone 
• 39755-03-8 4-hydroxy-1-phenyl-butan-1-one 
• 24070-52-8 4-bromo-1-phenyl-1-butanone 

Relevant academic research and scientific papers

Asymmetric synthesis of α-acyl-γ-butyrolactones possessing all-carbon quaternary stereocenters by phase-transfer-catalyzed alkylation

The enantioselective construction of all-carbon quaternary stereocenters on α-acyl-γ-butyrolactones has been achieved by the N-spiro chiral quaternary ammonium bromide 1-catalyzed alkylation under mild phase-transfer conditions. The resulting α-alkylated

α-Amino-α-vinyl-γ-butyrolactone derivatives from α-{[(trimethylsilyl)-methyl]alkylidene}-γ-butyrolactones

N-Protected α-amino-α-vinyl-γ-butyrolactones 1 are obtained by the aza-Michael-type addition of NsONHCO2Et to novel silylated α-ylidene-γ-butyrolactones 2, through ring opening of the intermediate aziridine and loss of the trimethylsilyl group.

Br?nsted Acid-Catalyzed Carbonyl-Olefin Metathesis inside a Self-Assembled Supramolecular Host

Carbonyl–olefin metathesis represents a powerful yet underdeveloped method for the formation of carbon–carbon bonds. So far, no Br?nsted acid based method for the catalytic carbonyl–olefin metathesis has been described. Herein, a cocatalytic system based on a simple Br?nsted acid (HCl) and a self-assembled supramolecular host is presented. The developed system compares well with the current benchmark catalyst for carbonyl–olefin metathesis in terms of substrate scope and yield of isolated product. Control experiments provide strong evidence that the reaction proceeds inside the cavity of the supramolecular host. A mechanistic probe indicates that a stepwise reaction mechanism is likely.

A palladium-catalyzed asymmetric allylic alkylation approach to α-quaternary γ-butyrolactones

The Pd-catalyzed asymmetric allylic alkylation (Pd-AAA) of enol carbonates derived from γ-butyrolactones is reported, affording the corresponding enantioenriched α,α′-disubstituted γ-butyrolactones in both high yields and high enantioselectivities (up to 94% ee). This method was eventually applied to the synthesis of chiral spirocyclic compounds.

Substrate range of the titanium TADDOLate catalyzed asymmetric fluorination of activated carbonyl compounds

The substrate range of the [TiCl2(TADDOLate)] (TADDOL=α,α,α′,α′-tetraaryl-1,3-dioxolane-4, 5-dimethanol)-catalyzed asymmetric α-fluorination of activated β-carbonyl compounds has been investigated. Optimal conditions for catalysis are characterized by using 5 mol-% of TiCl2(naphthalen-1- yl)-TADDOLate) as catalyst in a saturated (0.14 mol/l) MeCN solution of F-TEDA (1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis- [tetrafluoroborate]) at room temperature. A series of α-methylated β-keto esters (3-oxobutanoates, 3-oxopentanoates) with bulky benzyl ester groups (60-90% ee) or phenyl ester (67-88% ee) have been fluorinated readily, whereas α-acyl lactones were also readily fluorinated, but gave lower inductions (13-46% ee). Double stereochemical differentiation in β-keto esters with chiral ester groups raised the stereoselectivity to a diastereomeric ratio (dr) of up to 96.5:3.5. For the first time, β-keto S-thioesters were asymmetrically fluorinated (62-91.5% ee) and chlorinated (83% ee). Lower inductions were observed in fluorinations of 1,3-diketones (up to 40% ee) and β-keto amides (up to 59% ee). General strategies for preparing activated β-carbonyl compounds as important model substrates for asymmetric catalytic α-functionalizations are presented (>60 examples). Copyright

Formal [4+1] annulation of cyclopropyl amides and water mediated by Lewis acid: A novel entry to γ-butyrolactones

An efficient one-pot synthesis of substituted -butyrolactones from cyclopropyl amides mediated by the Lewis acid SnClH is reported. A mechanism involving a tandem ring-opening reaction and intramolecular cyclization reaction is proposed. Georg Thieme Verlag Stuttgart · New York.

Reductive Reformatsky-Honda reaction of α,β-unsaturated esters: Facile formation of 1,3-dicarbonyl compounds and β-hydroxy esters

The reaction of tris(triphenylphosphine)rhodium chloride [RhCl(PPh 3)3] with diethylzinc (Et2Zn) easily afforded a rhodium-hydride complex that effects the 1,4-reduction of α,β- unsaturated esters to give rhodium enolates. Formation of the rhodium enolate is followed by transmetalation with the zinc species to give a Reformatsky-type reagent, and this reacts with various acid chlorides at the α-position to give β-keto esters. The Reformatsky-type reagent also reacts with various electrophiles such as aldehydes, ketones and acid anhydrides to give the corresponding products in which the electrophiles were introduced reductively at the α-position of α,β-unsaturated esters. Copyright

Highly diastereo- and enantioselective Mannich reaction of lactones with N-Boc-aldimines catalyzed by bifunctional rosin-derived amine thiourea catalysts

A highly efficient diastereo- and enantioselective Mannich reaction of lactones with a variety of N-Boc-aldimines by using bifunctional rosin-derived amine thiourea catalysts was investigated for the first time, in general, affording the adducts bearing q

Oxidation products of 2-acyl-4,5-dihydrofurans

2-Benzoyl-4,5-dihydrofuran (5) readily undergoes oxidation in air, during chromatography on silica, or following exposure to oxidising agents (MCPBA, DMDO), to give 2-benzoylbutyrolactone (6) and tricycle 7 as the major products.

Unexpected reaction of a dimethylzinc-generated THF radical with aldehydes

A dimethylzinc-air-generated THF radical reacted with aldehydes at the β-position of an α-oxygenated THF.