106262-48-0

Upstream product

• 6790-38-1 1,2-epoxy-3-vinylpropane 
• 100-56-1 phenylmercury(II) chloride 
• 88842-13-1 (Z-)-ethyl 5-phenylpent-2-enoate 
• 16900-77-9 5-phenyl-2-pentynol 
• 104-53-0 3-phenyl-propionaldehyde 
• 930-22-3 epoxybutene 
• 2549-99-7 benzyl triethoxysilane 
• 50-00-0 formaldehyd 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 16520-62-0 4-Phenyl-1-butyne 
• 26429-96-9 (Z)-5-phenyl-2-pentenoic acid methyl ester 
• 129042-95-1 methyl 5-phenylpent-2-enoate 
• 93888-06-3 1-(oxiran-2-yl)-3-phenylpropan-1-ol 
• 37904-38-4 5-phenylpent-1-en-3-ol 

Downstream Products

• 125303-61-9 [(2S,3S)-3-phenethyloxiran-2-yl]methanol 
• 154428-47-4 (2R,3R)-trans-2,3-epoxy-5-phenyl-1-pentanol 
• 112087-56-6 (2Z)-5-phenylpent-2-enal 
• 33046-84-3 (2E)-5-phenyl-2-pentenal 
• 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 
• 36884-28-3 5-phenyl-1-pentanal 

Relevant academic research and scientific papers

An extremely mild desulfurization of thiiranes: An efficient transformation from geraniol to (+)- and (-)-linalool

Thiirane was transformed to alkene very efficiently at -78°C by triethylborane initiated radical reaction with tributyltin hydride. Enantiomerically pure (+)- and (-)-linalools were derived from geraniol in four steps including the alkene formation reaction.

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.

Simple cis-epoxide-based inhibitors of HIV-1 protease

The 4-nitrophenoxy-based epoxide 6a, conveniently synthesized using Sharpless epoxidation chemistry, has been shown to be an irreversible inhibitor of HIV-1 protease (k(inact) 1.8 μM, pH 6.5, I = 0.1 M). Related analogues, differing in the mode of attachm

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.

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

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.