320399-48-2

Upstream product

• 164072-67-7 (Z)-5-dimethylphenylsilyl-4-penten-1-ol 
• 627-27-0 homoalylic alcohol 
• 274676-28-7 allylbenzhydryldimethylsilane 
• 75-21-8 oxirane 
• 1078644-01-5 C₁₁H₁₅ISi 
• 198411-11-9 5-dimethylphenylsilyl-1-(2-tetrahydropyranyloxy)-4-pentyne 
• 821-09-0 n-Pent-4-enyl alcohol 
• 3839-31-4 dimethyl(phenyl)silyllithium 
• 5390-04-5 pent-1-yn-5-ol 
• 62992-46-5 1-(tetrahydropyranyloxy)-4-pentyn 
• 97-99-4 Tetrahydrofurfuryl alcohol 

Downstream Products

• 1078644-04-8 C₁₉H₃₄OSi₂ 

Relevant academic research and scientific papers

Regioselective and stereoselective synthesis of tetrahydrofurans from a functionalized allylic silane and an aldehyde via formal [3+2]-cycloaddition reaction

Allylsilanes are known as useful reagents for the stereoselective formation of ring systems. Previous studies have shown that tetrahydrofurans can be constructed via formal [3+2]-cycloadditions of aldehydes and allylsilanes. A new challenge is to understand the intermediate, after a nucleophile attacks a carbonyl activated by the Lewis acid, in which two silyl-protected alkoxy groups with chemical equivalency could undergo formal cycloaddition reaction to afford a disubstituted and/or a trisubstituted tetrahydrofuran. Preparation of the protected α-hydroxy aldehyde and a functionalized allylic silane is discussed, as well as their formal cycloaddition reaction to form tetrahydrofurans.

Cp2TiCl2-catalyzed regio- and chemoselective one-step synthesis of γ-substituted allylsilanes from terminal alkenes using dianion-type zincate (SiSiNOL-Zn-ate)

A regio-/chemoselective silylation reaction of various functionalized terminal alkenes in the presence of titanocene dichloride, based on a newly designed dianion-type zincate, was developed. The present silylation of terminal alkenes is a powerful tool f

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.

Silicon-Directed Cyclization of Vinylsilanes Bearing Hydroxy Group Catalyzed by an Acid

Silicon-directed stereoselective syn addition of hydroxy group to olefinic double bond occurs intramolecularly in an acid-catalyzed cyclization of vinylsilanes bearing hydroxy group.Thus 5-dimethylphenylsilyl-4-penten-1-ol is smoothly cyclized to 2-(dimethylphenylsilyl)methyltetrahydrofuran upon the treatment of a catalytic amount of p-toluenesulfonic acid (TsOH) or TiCl4.