58649-05-1

Upstream product

• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 62-53-3 aniline 
• 94-41-7 benzalacetophenone 
• 145473-85-4 (Z)-2,2-Dimethyl-3,5-diphenyl-5-trimethylsilanyloxy-pent-4-enoic acid methyl ester 

Downstream Products

• 861310-55-6 5-benzoyl-3,3-dimethyl-4-phenyl-3H-furan-2-one 

Relevant academic research and scientific papers

Cage Like Al-KIT-5 Mesoporous Materials for C-C Bond Formation Reactions under Solvent Free Conditions

The C-C bond forming reactions are of fundamental importance in chemistry. As a result there is ever growing interest for chemists to develop new methods for C-C bond formation. We report here three dimensional nano-cage mesoporous aluminosilicate materia

Pentafluorophenylammonium trifluoromethanesulfonimide: Mild, powerful, and robust catalyst for mukaiyama aldol and mannich reactions between ketene silyl acetals and ketones or oxime ethers

Pentafluorophenylammonium trifluoromethanesulfonimide (C6F 5N+H3·NTf2-) promotes Mukaiyama aldol and Mannich reactions using ketene silyl acetals with ketones and oxime ethers, respectively. The prese

NO cations as highly efficient catalysts for carbon-carbon bond forming reactions

NO cations were found to be a highly effective catalysts in several carbon-carbon bond forming reactions. For example, [3 + 2] cycloadditions of nitrones or azomethine imines with vinyl ethers proceeded in the presence of 0.1-1 mol % of the NO cation to afford the desired adducts in high yields. Copyright

Lewis base-catalyzed Michael reactions between trimethylsilyl enolate and α,β-unsaturated carbonyl compounds

Michael reactions between trimethylsilyl enolates and α,β- unsaturated carbonyl compounds by using a Lewis base catalyst such as lithium benzamide 4 or lithium succinimide 5 in DMF proceeded smoothly to afford the corresponding Michael-adducts in good to high yields (Tables 1-3). In order to extend the scope, Michael reactions catalyzed by lithium acetate (AcOLi), a weak and readily available Lewis base, were studied in detail. AcOLi behaved as an effective Lewis base catalyst in Michael reactions between trimethylsilyl enolates and α,β-unsaturated carbonyl compounds at 0 °C or at room temperature (Tables 4-6). Hindered α,β-unsaturated ketones behaved as excellent Michael-acceptors in the above reaction at room temperature (Table 5). This catalytic Michael reaction also proceeds smoothly in the presence of other lithium carboxylates that are easily prepared in situ by treating carboxylic acids with lithium carbonate (LE2CO3) (Scheme 2). This is the first example of Lewis base-catalyzed Michael reactions between α,β-unsaturated carbonyl compounds and trimethylsilyl enolates.

An efficient synthesis of 3,4-dihydropyran-2-one derivatives by Lewis base-catalyzed tandem Michael addition and lactonization

A convenient one-pot preparation of 3,4-dihydropyran-2-one derivatives by Michael addition of silyl enolate derived from phenyl ester with α,β-unsaturated ketones in the presence of a Lewis base catalyst such as tetrabutylammonium phenoxide was developed. In this catalytic cycle, 3,4-dihydropyran-2-ones were produced in good to excellent yields via intramolecular cyclization of in situ formed Michael-adducts.

Lithium acetate-catalyzed Michael reaction between trimethylsilyl enolate and α,β-unsaturated carbonyl compound

Lithium acetate-catalyzed Michael reaction between trimethylsilyl enolates and α,β-unsaturated carbonyl compounds in DMF proceeded smoothly to afford the corresponding Michael-adducts in good to high yields. Hindered α,β-unsaturated ketones also behaved as an excellent Michael-acceptor in the above reaction at room temperature.

Lewis base catalyzed Michael reaction between ketene silyl acetals and α,β-unsaturated carbonyl compounds

Catalytic Michael reaction between trimethylsilyl enolates and α,β-unsaturated carbonyl compounds by using a Lewis base such as lithium benzamide or lithium succimide in a DMF solvent proceeded smoothly to afford the corresponding Michael adducts.

Spontaneous aldol and Michael additions of simple enoxytrimethylsilanes in DMSO

Activation of simple trimethylsilyl ketene acetals by dipolar aprotic solvents has been evidenced, allowing efficient solvent assisted aldol and Michael additions under extremely simple, mild and metal free conditions. (C) 2000 Elsevier Science Ltd.

Lanthanide trifluoromethanesulfonates as reusable catalysts. Michael and Diels-Alder reactions

The Michael reaction of silyl enolates with α,β-unsaturated ketones and the Diels-Alder reaction of carbonyl containing dienophiles are catalyzed by a catalytic amount of lanthanide trifluoromethanesulfonate to give the corresponding adducts in high yields. In both reactions, the catalyst can be recovered and reused.