39520-63-3

Upstream product

• 6790-38-1 1,2-epoxy-3-vinylpropane 
• 100-56-1 phenylmercury(II) chloride 
• 74940-41-3 1-(tributylstannyl)-5-phenyl-2-pentene 
• 16900-77-9 5-phenyl-2-pentynol 
• 104-53-0 3-phenyl-propionaldehyde 
• 50-00-0 formaldehyd 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 930-22-3 epoxybutene 
• 2549-99-7 benzyl triethoxysilane 
• 16520-62-0 4-Phenyl-1-butyne 
• 26429-96-9 (Z)-5-phenyl-2-pentenoic acid methyl ester 
• 88842-13-1 (Z-)-ethyl 5-phenylpent-2-enoate 
• 129042-95-1 methyl 5-phenylpent-2-enoate 
• 93888-06-3 1-(oxiran-2-yl)-3-phenylpropan-1-ol 

Downstream Products

• 112087-56-6 (2Z)-5-phenylpent-2-enal 
• 33046-84-3 (2E)-5-phenyl-2-pentenal 
• 850306-78-4 phenethylallyl methyl carbonate 
• 1318801-84-1 (Z)-3-iodo-5-phenylpent-2-en-1-ol 
• 1318801-85-2 (Z)-3-iodo-5-phenylpent-2-enal 
• 1318801-75-0 C₁₅H₁₆O₂ 
• 1318801-86-3 C₁₂H₁₃I 
• 1318801-69-2 (Z)-4-phenethylhepta-4,6-diene-2,3-dione 
• 1318801-74-9 C₁₅H₁₆O₂ 
• 129413-75-8 C₁₁H₁₃Br 

Relevant academic research and scientific papers

Stereoselective Carbocyclization of Vinyloxiranes Catalyzed by Lewis Acids: Construction of the Musellarin Tricyclic Core

Stereoselective carbocyclizations of vinyloxiranes were efficiently catalyzed by Lewis acids to provide cyclic homoallyl alcohols as single isomers. The choice of Lewis acid, B(C6F5)3 was crucial for the stereoselective tr

Iridium-Catalyzed Regioselective Hydroalkynylation of Internal Alkenes Directed by an Oxime

We report here an iridium-catalyzed hydroalkynylation of allylic alcohols protected by an oxime group. Catalytic alkynylation occurs exclusively at the distal position of the alkene. This method generates γ-alkynyl alcohol oximes directly from internal alkenes and terminal alkynes. The oxime group can be readily removed to afford a free alcohol, thus providing an indirect route for the catalytic hydroalkynylation of allylic alcohols.

Cascade reaction including a formal [5?+?2] cycloaddition by use of alkyne-Co2(CO)6 complex

A new cascade reaction including formal [5 + 2] cycloaddition was developed. Treatment of homocinnamyl alcohol and Co2(CO)6-complexed arylpropynal with BF3·OEt2 resulted in the generation of hydrobenzocyclohepta

Acid-catalyzed chirality-transferring intramolecular Friedel-Crafts cyclization of α-hydroxy-α-alkenylsilanes

Acid-catalyzed intramolecular Friedel-Crafts cyclization of optically active α-hydroxy-α-alkenylsilanes possessing a benzene ring (>99% ee) with TMSOTf as a Lewis acid gave enantio-enriched tetrahydronaphthalenes (up to 98% ee). The silyl group attached to the chiral carbon played a crucial role in the chirality transfer.

Tandem Catalysis: Transforming Alcohols to Alkenes by Oxidative Dehydroxymethylation

We report a Rh-catalyst for accessing olefins from primary alcohols by a C-C bond cleavage that results in dehomologation. This functional group interconversion proceeds by an oxidation-dehydroformylation enabled by N,N-dimethylacrylamide as a sacrificial acceptor of hydrogen gas. Alcohols with diverse functionality and structure undergo oxidative dehydroxymethylation to access the corresponding olefins. Our catalyst protocol enables a two-step semisynthesis of (+)-yohimbenone and dehomologation of feedstock olefins.

Regioselective Ni-Catalyzed Carboxylation of Allylic and Propargylic Alcohols with Carbon Dioxide

An efficient Ni-catalyzed reductive carboxylation of allylic alcohols with CO2 has been successfully developed, providing linear β,γ-unsaturated carboxylic acids as the sole regioisomer with generally high E/Z stereoselectivity. In addition, the carboxylic acids can be generated from propargylic alcohols via hydrogenation to give allylic alcohol intermediates, followed by carboxylation. A preliminary mechanistic investigation suggests that the hydrogenation step is made possible by a Ni hydride intermediate produced by a hydrogen atom transfer from water.

Titanocene(III) chloride mediated radical-induced opening of monosubstituted epoxy acetates for the synthesis of primary allylic alcohols

A simple and efficient method for the synthesis of primary allylic alcohols from monosubstituted epoxy acetates has been developed using titanocene(III) chloride mediated epoxide ring opening via acetate elimination.

Ring Expansion of Epoxides under Br?nsted Base Catalysis: Formal [3+2] Cycloaddition of β,γ-Epoxy Esters with Imines Providing 2,4,5-Trisubstituted 1,3-Oxazolidines

A novel ring-expansion reaction of epoxides under Br?nsted base catalysis was developed. The formal [3+2] cycloaddition reaction of β,γ-epoxy esters with imines proceeds in the presence of triazabicyclodecene (TBD) as a superior Br?nsted base catalyst to afford 2,4,5-trisubstituted 1,3-oxazolidines in a highly diastereoselective manner. This reaction involves the ring opening of the epoxides with the aid of the Br?nsted base catalyst to generate α,β-unsaturated esters having an alkoxide at the allylic position, which would formally serve as a synthetic equivalent of the 1,3-dipole, followed by a cycloaddition reaction with imines in a stepwise fashion. This methodology enables the facile synthesis of enantioenriched 1,3-oxazolidines from easily accessible enantioenriched epoxides.

Copper-catalyzed enantioselective allylic alkylation of terminal alkyne pronucleophiles

The copper-catalyzed enantioselective allylic alkylation of terminal alkynes with primary allylic phosphates was developed by the use of a new chiral N-heterocyclic carbene ligand bearing a phenolic hydroxy group at the ortho position of one of the two N-aryl groups. This reaction occurred with excellent γ-branch regioselectivity and high enantioselectivity, forming a controlled stereogenic center at the allylic/propargylic position. Various terminal alkynes, including silyl, aliphatic, and aromatic alkynes, could be used directly without premetalation of the C(sp)-H bond. On the basis of the results of experiments using an isomeric secondary allylic phosphate, which gave a branched product through an α-selective substitution reaction with retention of configuration, a reaction pathway involving 1,3-allylic migration of Cu in a ([σ + π]-allyl)copper(III) species is proposed.

Copper-catalyzed enantioselective allylic substitution with alkylboranes

The first catalytic enantioselective allylic substitution reaction with alkylboron compounds has been achieved. The reaction between alkyl-9-BBN reagents and primary allylic chlorides proceeded with excellent γ-selectivities and high enantioselectivities under catalysis of a Cu(I)-DTBM-SEGPHOS system. The protocol produces terminal alkenes with an allylic stereogenic center branched with functionalized sp3-alkyl groups. The reaction with a γ-silicon-substituted allyl chloride affords an efficient strategy for the enantioselective synthesis of functionalized α-stereogenic chiral allylsilanes.