137438-47-2

Upstream product

• 4362-48-5 2-cyclohexyl-1,3-dioxolane 
• 14642-79-6 benzyloxy-trimethylsilane 
• 762-72-1 allyl-trimethyl-silane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 100-51-6 benzyl alcohol 
• 176038-69-0 phenylmethanol 
• 100-52-7 benzaldehyde 
• 69036-26-6 1-cyclohexyl-3-buten-1-ol 
• 100-39-0 benzyl bromide 

Relevant academic research and scientific papers

Silicomolybdic acid supported on silica gel: An efficient catalyst for Hosomi-Sakurai reactions

Silicomolybdic acid that is supported on silica gel (50 wt %) efficiently catalyzes the high-yielding Hosomi-Sakurai allylation of carbonyl compounds by allyltrimethylsilane in the presence of benzyl alcohol. The reaction rates of inactive substrates and the yields were greatly increased when preformed acetals were used as substrates.

Bronsted acid-catalyzed three-component hosomi-sakurai reactions

Aldehydes react with silyl ethers or the corresponding alcohols and allylsilanes in the presence of catalytic amounts of 2,4-dinitrobenzenesulfonic acid (DNBA) to provide a wide range of homoallylic ethers in moderate to high yields.

Iron(III) chloride-catalyzed convenient one-pot synthesis of homoallyl benzyl ethers starting from aldehydes

(Matrix presented) Iron(III) chloride-catalyzed effective allylation reactions of acetals with allyltrimethylsilane proceeded smoothly in high to excellent yields. In addition, this method could be applied to the one-pot synthesis of homoallyl benzyl ethe

Catalytic allylation of aldehydes with allyltrimethylsilane using in situ-generated trimethylsilyl methanesulfonate (TMSOMs) as a catalyst

One-pot allylation reactions of carbonyl compounds with allyltrimethylsilane catalyzed by in situ-generated TMSOMs were carried out. TMSOMs was found to be an efficient catalyst in the allylation of the hydrates of α-keto aldehyde and glyoxylate. In situ-generated TMSOMs also can catalyze the SMS reaction of the aldehydes giving the functionalized homoallylic ethers in good to excellent yields.

Novel reactions of ethylene acetals with silyl-substituted nucleophiles. A mild and efficient procedure for the synthesis of homoallyl alkyl ethers and unsymmetrical dialkyl ethers

Efficient one-pot synthesis of homoallyl alkyl ethers and dialkyl ethers was performed by the allylation and reduction of ethylene acetals with allyltrimethylsilane and t-butyldimethylsilane, respectively, in the presence of alkoxytrimethylsilane.

Highly diastereoselective intramolecular allylation reactions of mixed silyl-substituted acetals

The reaction of preformed mixed acetals derived from (α-hydroxyalkyl)dimethylallylsilane with a number of aromatic and aliphatic aldehydes in the presence of Lewis acids results in a highly diastereoselective intramolecular allylation reaction. The reaction proceeds through a cyclic synclinal SE′ addition of the allylsilane to an intermediate oxocarbenium ion. The reaction occurs exclusively by an intramolecular process as determined by means of a cross-over experiment. The relative stereochemistry was determined by the conversion of one of the allylation products to a known (stereodefined) aldol-type product. A greater degree of diastereoselectivity is obtained by in-situ formation of an oxocarbenium ion from (α-hydroxyhexyl)dimethylallylsilane and an aldehyde in the presence of boron trifluoride etherate. The diastereoselectivity of the in-situ allylation reaction typically exceeds 100:1 in favor of the syn adduct. However, reactions with electron rich aryl aldehydes resulted in a diminished degree of diastereoselectivity. The initial product of the in-situ reaction is an unstable silyl fluoride which is readily hydrolyzed to a silanol derivative upon reaction with methanolic potassium hydroxide. The overall yield of the two-step process is greater than 80%. A method for the synthesis of more highly substituted (α-alkoxyalkyl)dimethylallylsilanes by allyl anion displacement of methoxide from silicon is also described. The methyl siloxane derivatives were obtained by ozonolytic cleavage of an unsubstituted allyl group in methanol.

Oxidative Cleavage of Mono-, Di-, and Trisubstituted Olefins to Methyl Esters through Ozonolysis in Methanolic NaOH

The ozonolysis of alkenes in methanolic NaOH or NaOMe with CH2Cl2 as cosolvent leads directly to methyl esters.The procedure has been used to prepare various α-, β-, and ω-alkoxy esters, acyloxy esters, and α- and β-N-acyl and N-sulfonyl esters from appropriate unsaturated ethers, esters and amides.Other examples include the formation of dimethyl octanedioate from cyclooctene (75percent yield), dimethyl nonanedioate and methyl nonaoate from methyl oleate (77 and 78percent, respectively), and tetradecanoic acid γ-lactone from 2-methyl-2-hexadecen-6-ol (80percent yield).

The Silyl Modified Sakurai (SMS) reaction. An efficient and versatile one-pot synthesis of homoallylic ethers

An efficient and versatile preparation of homoallylic ethers from trimethylsilyl ethers, allyltrimethylsilane and carbonyl compounds is described. Some preliminary experiments, aimed at controlling the diastereofacial selection in the SMS reaction, are al