460752-11-8

Upstream product

• 100-52-7 benzaldehyde 
• 3174-74-1 dihydropyran 
• 1743-36-8 1-phenylbut-3-yn-1-ol 
• 110-87-2 3,4-dihydro-2H-pyran 

Downstream Products

• 460752-21-0 4-benzyldimethylsilyl-1-phenyl-1-(2-tetrahydropyranyloxy)-3-butyne 
• 460752-20-9 4-dimethylphenylsilyl-1-phenyl-1-(2-tetrahydropyranyloxy)-3-butyne 
• 4660-19-9 5-hydroxy-5-phenyl-pent-2-ynoic acid methyl ester 
• 35390-18-2 1-phenyl-3-hexyn-1-ol 
• 1041333-86-1 5-hydroxy-5-phenyl-pent-2-ynoic acid ethyl ester 
• 1274824-03-1 3-[2-phenyl(tetrahydro-2H-pyran-2-yloxy)ethyl]pyrano-[3',4':4,5]imidazo[1,2-a]pyridin-1-one 
• 460752-86-7 (Z)-4-benzyldimethylsilyl-1-phenyl-3-octen-1-ol 
• 460752-85-6 (Z)-4-dimethylphenylsilyl-1-phenyl-3-octen-1-ol 
• 460752-52-7 (E)-4-benzyldimethylsilyl-4-bromo-1-phenyl-1-(2-tetrahydropyranyloxy)-3-butene 

Relevant academic research and scientific papers

Acyloxy Rearrangement-Triggered Regioselective Hydration of ?-Acetoxy-α,β-Alkynoates/Halo Alkynes

Herein, we report a simple, efficient, highly regioselective, and broad-scope hydration method that is facilitated by an unusual interception of an electrophilic intermediate by water generated via acetate group participation during [3,3]-acyloxy rearrang

Ruthenium Hydride Catalyzed Silylvinylation of Internal Alkynes Using Ethylene as an Additive

An efficient synthetic strategy for the regiospecific silylvinylation of internal alkynes is described. This transformation is catalyzed by RuHCl(CO)(SIMes)PPh3 and provides a net 5-exo-dig trans-silylvinylation of internal alkynes. Ethylene wa

Ruthenium-catalyzed [2 + 2] cycloadditions between norbornene and propargylic alcohols or their derivatives

Diastereoselective ruthenium-catalyzed [2 + 2] cycloadditions of norbornene and propargylic alcohols or their derivatives were investigated. The cycloadditions were found to be highly stereoselective, giving exo cycloadducts in moderate to excellent yields with diastereoselectivities up to 92:8. When a chiral propargylic alcohol was used in the cycloaddition, up to 80% ee of the [2 + 2] cycloadducts was observed after oxidation of the alcohol.

1,2-Silyl-migrative cyclization of vinylsilanes bearing a hydroxy group: Stereoselective synthesis of multisubstituted tetrahydropyrans and tetrahydrofurans

Acid-catalyzed intramolecular addition of a hydroxy group to α-alkylated vinylsilanes has been studied. Treatment of (Z)-5-alkyl-5-silyl-4-penten-1-ols 1 (R = alkyl) with 5 mol % TiCl4 in CHCl3 gave trans-2-alkyl-3-silyltetrahydropyrans 2 exclusively (trans/cis = > 99/1 to 97/3). The cyclization efficiency and rate strongly depended on the geometry of the C-C double bond and the silyl group. The use of (E)-vinylsilanes resulted in lower yields with poor cis-selectivity. In the cyclization of (Z)-1 (R = Bu), the silyl group used, the reaction time, and the yield of 2 were as follows: SiMe2Ph, 9.5 h, 75%; SiMe3, 7.5 h, 66%; SiMePh2, 24 h, 58%; SiMe2-t-Bu, 0.75 h, 85%; SiMe2Bn, 1.5 h, 78%. This 1,2-silyl-migrative cyclization could be applied to stereoselective synthesis of trisubstituted tetrahydropyrans. The acid-catalyzed reaction of 1-, 2-, or 3-substituted (Z)-5-silyl-4-nonen-1-ols 8 gave r-2,t-3,c-6-, r-2,t-3,t-5-, or r-2,t-3,c-4-trisubstituted tetrahydropyrans with high diastereo-selectivity, respectively. (Z)-4-Alkyl-4-silyl-3-buten-1-ols 5 as well as 1 underwent the 1,2-silylmigrative cyclization to give 2-alkyl-3-silyltetrahydrofurans 6 with high trans-selectivity. This silicon-directed cyclization was also available for the stereoselective synthesis of tri- and tetrasubstituted tetrahydrofurans.