91153-93-4

Upstream product

• 110-65-6 1,4-dihydroxybut-2-yne 
• 100-58-3 phenylmagnesium bromide 
• 1159837-56-5 1,2-dihydroxy-2-phenyl-3-butene 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 100-52-7 benzaldehyde 
• 1459246-62-8 4-phenyl-4-vinyl-1,3-dioxolan -2-one 
• 108-86-1 bromobenzene 

Downstream Products

• 20946-89-8 1-tert-butyl-3-phenyl-1H-pyrrole 
• 53646-85-8 1,3-diphenyl-1H-pyrrole 
• 53646-88-1 1-benzyl-3-phenyl-1H-pyrrole 
• 1357182-62-7 (2E)-2-phenyl-but-2-ene-1,4-diol bis-trichloroacetimidate 
• 1357182-73-0 tert-butyl [1-(hydroxymethyl)-1-phenylprop-2-en-1-yl]carbamate 
• 1357182-68-3 4-phenyl-4-vinyl-2-(trichloromethyl)oxazoline 
• 1357182-80-9 4-(1-phenylvinyl)-2-(trichloromethyl)oxazoline 

Relevant academic research and scientific papers

Copper-Mediated SN2′ Allyl-Alkyl and Allyl-Boryl Couplings of Vinyl Cyclic Carbonates

A method for the copper-catalyzed borylmethylation and borylation of vinyl cyclic carbonates through an SN2′ mechanism is reported. These singular reactions involve selective SN2′ allylic substitutions with concomitant ring opening of the cyclic carbonate and with extrusion of CO2 and formation of a useful hydroxyl functionality in a single step. The stereoselectivity of the homoallylic borylation and allylic borylation processes can be controlled, and synthetically useful unsaturated (E)-pent-2-ene-1,5-diols and (E)-but-2-ene-1,4-diols are accessed.

C-quaternary vinylglycinols by metal-catalyzed cyclization of allylic bistrichloroacetimidates

Bistrichloroacetimidates derived from 2-substituted but-2-ene-1,4-diols are transformed into 4-substituted 4-vinyloxazolines in high yields and excellent regioselectivities when Lewis acids AlCl3, FeCl3, TMSOTf, BF3OEt2, and AgBF4 are used as catalysts as well as with the Pd(PPh3)2Cl2/AgBF4 catalytic system. Lower regioselectivity is achieved with a neutral PdCl 2(MeCN)2 catalyst and this could be a consequence of a switch to a competitive but less selective reaction mechanism. It is demonstrated that 4-substituted 4-vinyloxazolines can be efficiently transformed to N-Boc-protected C-quaternary vinylglycinols in a one-pot procedure. Georg Thieme Verlag Stuttgart · New York.

Grignard Addition Reactions to 1,4-Difunctionalized But-2-ynes

Trisubstituted alkenes of E geometry have been prepared by anti addition of Grignard reagents to 1,4-difunctionalized but-2-ynes.Addition of primary, secondary and aromatic Grignard reagents to but-2-yne-1,4-diol provided (E)-2-substituted but-2-ene-1,4-diols as major products along with the corresponding 2-substituted buta-2,3-dien-1-ols.Addition of phenylmagnesium bromide to the mono- and di-methyl ethers of but-2-yne-1,4-diol gave 2,3-diphenyl-1,3-diene.Treatment of 4-dimethylaminobut-2-yn-1-ol with primary alkyl and alkenyl Grignard reagents afforded the 2-substituted anti addition product regiospecifically, stereospecifically and in high yield.Reaction of 1-dimethylamino-4-methoxybut-2-yne with butylmagnesium bromide provided only the 3-substituted anti addition product in good yield.

A NEW SYNTHESIS OF trans-2-SUBSTITUTED-2-BUTENE-1,4-DIOLS FROM 2-BUTYNE-1,4-DIOL VIA NUCLEOPHILIC ADDITION OF GRIGNARD REAGENTS

trans-2-Substituted-2-butene-1,4-diols were readily obtained by reactions of 2-butyne-1,4-diol with Grignard reagents in good yields.