128372-48-5

Upstream product

• 591-50-4 iodobenzene 
• 6117-80-2 1,4-butenediol 
• 100-52-7 benzaldehyde 
• 107-02-8 acrolein 
• 1008-73-7 4-phenyldihydrofuran-2(3H)-one 
• 153867-09-5 2,2-Dimethyl-5-phenyl-4,5-dihydro-[1,3]dioxepine 

Downstream Products

• 1008-73-7 4-phenyldihydrofuran-2(3H)-one 
• 1376349-15-3 C₁₄H₁₇BrO₂ 
• 1376348-33-2 (E)-ethyl 6-bromo-5-phenylhex-2-enoate 

Relevant academic research and scientific papers

Formal [4 + 1]- and [5 + 1]-annulation by an SN2-conjugate addition sequence: Stereoselective synthesis of highly substituted carbocycles

K2CO3-mediated reactions of 6-bromo-2-hexenoates and 7-bromo-2-heptenoate with active methylene compounds deliver highly substituted cyclopentane and cyclohexane derivatives, respectively via a sequence of S N2-conjugate a

Stereoselective Substitution at Phenyl-Substituted γ-Lactols with Organometallic Compounds

A variety of monosubstituted γ-lactols 4-6 were prepared in good yields by DIBAL reduction of the corresponding γ-lactones 1-3.The monophenyl-substituted lactols 4b-6b were transformed into disubstituted tetrahydrofuran derivatives by replacement of the hydroxyl group by the alkyl residue of organometallic compounds used as nucleophiles.The diastereoselectivity of the substitution was found to depend strongly on the substitution pattern of the γ-lactols.For the reaction of the 3- and 4-substituted derivatives 4b and 5b, respectively, good to excellent trans selectivity was observed, while the 5-substituted derivative reacted without any diastereoselectivity.These results were interpreted by means of the Felkin-Anh model. - Keywords: γ-Lactone / Reduction / γ-Lactol / Lewis acid / Tetrahydrofurans

A FACILE SYNTHESIS OF 4-ARYLBUTYROLACTONES VIA THE PALLADIUM-CATALYZED ARYLATION OF 1,3-DIOXEP-5-ENE

1,3-Dioxep-5-ene was arylated by using Heck reaction, and the arylated 1,3-dioxep-5-ene derivatives were easily converted into 4-arylbutyrolactones, intermediates for the synthesis of natural products and biological active compounds.

β-vinyl-γ-butyrolactones via the palladium-catalysed reaction of vinyl triflates with Z-2-buten-1,4-diol

The palladium-catalysed reaction of vinyl triflates with Z-2-buten-1,4-diol affords β-vinyl-γ-butyrolactols (4-vinyl-2-hydroxy-tetrahydrofurans) which are converted into the corresponding β-vinyl-γ-butyrolactones by a smooth oxidation with Ag2C