66049-99-8

Upstream product

• 93617-31-3 exo benzyl-5 oxa-4 endo tricyclo<5.2.1.0^2,6>decene-8 one-3 
• 78905-97-2 (E)-5-phenylpent-3-enoic acid 
• 122-78-1 phenylacetaldehyde 
• 6052-66-0 1-phenyl-3-buten-2-ol 
• 100-39-0 benzyl bromide 
• 107409-09-6 (Z)-2,5-dihydroxy-1-phenylpent-3-ene 

Downstream Products

• 111853-64-6 5-benzylfuran-2(3H)-one 
• 3183-15-1 4-oxo-5-phenylvaleric acid 
• 1436857-06-5 (4R,5S)-5-benzyl-4-(dimethyl(phenyl)silyl)dihydrofuran-2(3H)-one 

Relevant academic research and scientific papers

Catalytic use of selenium electrophiles in cyclizations

A new and convenient one-pot method for a catalytic addition-elimination reaction using selenium electrophiles has been developed. In the presence of 5 mol % diphenyl diselenide, [bis(trifluoroacetoxy)iodo]benzene in acetonitrile converted a range of (E)-3-butenoic acids into the corresponding butenolides in good yields.

A facile synthesis of γ-butenolides via cyclization of 3-alkenoic acids with dimethyl sulfoxide and oxalyl bromide

The combination of dimethyl sulfoxide and oxalyl bromide was used to accomplish the cyclization of 3-alkenoic acids with the aid of a base to afford γ-butenolides, in which bromodimethylsulfonium salt generated in situ was proposed to serve as a Br+ source.

Mechanistic and Synthetic Investigations on the Dual Selenium-π-Acid/Photoredox Catalysis in the Context of the Aerobic Dehydrogenative Lactonization of Alkenoic Acids

The aerobic dehydrogenative lactonization of alkenoic acids facilitated by a cooperative nonmetallic catalyst pair is reported. The title procedure relies on the adjusted interplay of a photoredox and a selenium-π-acid catalyst, which allows for the regiocontrolled construction of five- and six-membered lactone rings in yields of up to 96%. Notable features of this method are pronounced efficiency and practicality, good functional group tolerance, and high sustainability, since ambient air and visible light are adequate for the clean conversion of alkenoic acids into their respective lactones. The title method has been used as a case study to elucidate the general mechanistic aspects of the dual selenium-π-acid/photoredox catalysis. On the basis of NMR spectroscopic, mass spectrometric, and computational investigations, a more detailed picture of the catalytic cycle is drawn and the potential role of trimeric selenonium cations as catalytically relevant species is discussed.

Lewis base-catalyzed electrophilic lactonization of selenyl bromide resin and facile solid-phase synthesis of furan-2(5H)-one derivatives

A facile solid-phase synthesis approach was developed for the rapid synthesis of multi-substituted furan-2(5H)-one derivatives libraries. The synthetic strategy included the selenyl bromide resin-induced electrophilic lactonization catalyzed by Lewis base, lithiation, nucleophilic substitution and oxidation-elimination of the selenium resins. The advantages of the new method are good yields, high purity, straightforward operations and high diversity of the products, lack of odor, and good stability of the selenium resins. Copyright

One-pot sequential 1,4- and 1,2-reductions of α,β-unsaturated δ-lactones to the corresponding δ-lactols with CuCl and NaBH 4 in methanol

An efficient, one-pot method for the highly chemoselective synthesis of δ-lactols from α,β-unsaturated δ-lactones using CuCl and NaBH4 in methanol was developed. Georg Thieme Verlag Stuttgart. New York.

Gold-catalyzed intramolecular oxidative cross-coupling of nonactivated arenes

(Chemical Equatation Reprentation An (Au)some coupling! Gold-catalyzed cascade C-O cyclizations of benzyl-substituted allenoate esters followed by intramolecular oxidative C-C cross-coupling involving aryl C-H functionalization were performed with Selectf

Pd-catalyzed 5-endo-trig-type cyclization of β,γ-unsaturated carbonyl compounds: An efficient ring closing reaction to give γ-butenolides and 3-pyrrolin-2-ones

The 5-endo-trig-type cyclization has been performed using a Pd-bis(isoxazoline) catalyst. The present cyclization of β,γ- unsaturated carbonyl compounds gave γ-butenolides and 3-pyrrolin-2-ones in good to excellent yields.

Gold-catalyzed cyclization of tert-butyl allenoate: General synthesis of 2,4-functionalized butenolides

AuCl3 efficiently catalyzes cyclization of tert-butyl allenoates into γ-butenolides. Advantage of directly using allenic ester precursor instead of corresponding acid is demonstrated in the synthesis of a variety of 2,4-disubstituted butenolides. A low catalyst loading and mild reaction condition makes this process an attractive alternative over conventional methods using strong Lewis acids.

NOUVELLE METHODE DE SYNTHESE DES γ-LACTONES ET (5H)FURANNONES-2-MONOSUBSTITUEES

3-monosubstituted γ-lactones and 5-mono- or 3,5-disubstituted 2-(5-H)-furanones have been prepared by the reaction of Grignard reagents with lactols.

EFFICIENT TRANSFORMATION OF (Z)-2-BUTENE-1,4-DIOLS TO α,β-BUTENOLIDES: A SIMPLE SYNTHESIS OF (+/-)-ELDANOLIDE

(Z)-2-Butene-1,4-diols are efficiently converted to the corresponding α,β-butenolides using silver carbonate/celite and this methodology has been applied to the synthesis of (+/-)-eldanolide, the wing gland pheromone of the male African sugar cane borer, Eldana saccharina (wlk).