320399-69-7

Upstream product

• 320400-08-6 5-dimethylphenylsilyl-3-phenyl-1-(2-tetrahydropyranyloxy)-4-pentyne 
• 3839-31-4 dimethyl(phenyl)silyl lithium 
• 57194-69-1 cinnamaldehyde 
• 220801-86-5 3-phenyl-4-pentyn-1-ol 
• 320399-95-9 3-phenyl-1-(2-tetrahydropyranyloxy)-4-pentyne 

Relevant academic research and scientific papers

Efficient access to polysubstituted tetrahydrofurans by electrophilic cyclization of vinylsilyl alcohols

Vinylsilyl alcohols undergo intramolecular cyclization to provide di-, tri- or tetrasubstituted-tetrahydrofurans. The influence of the number and position of substituents in the stereoselectivity of the process has been studied. Moreover, DFT calculations

Acid-catalyzed cyclization of vinylsilanes bearing a hydroxy group: A new method for stereoselective synthesis of disubstituted tetrahydrofurans

In the presence of a catalytic amount of TsOH or TiCl4, (Z)-5-silyl-4-penten-1-ols ((Z)-1) are smoothly cyclized to 2-silylmethyl-substituted tetrahydrofurans. This cyclization is applicable to the construction of a tetrahydropyran ring. The silyl group and the geometry of the C-C double bond strongly influence the cychzation rate. TBDMS and benzyldimethylsilyl groups considerably accelerate the cyclization in comparison with a dimethylphenylsilyl group, and (E)-vinylsilanes show much lower reactivity than the corresponding (Z)-isomers. The cyclization proceeds by stereospecific syn addition of the hydroxy group. Vinylsilanes 17, 19, and 21, (Z)-5-silyl-4-penten-1-ols bearing a substituent on the methylene tether, smoothly undergo the acid-catalyzed cyclization to give trans-2,5-, cis-2,4-, and trans-2,3-disubstituted tetrahydrofurans, respectively, with moderate to high stereoselectivity. The silyl group of some cychzed products can be easily converted into a hydroxy group with stereochemical retention.