25201-49-4

Upstream product

• 98-53-3 4-tercbutyl-cyclohexanone 
• 107-18-6 allyl alcohol 
• 106-95-6 allyl bromide 
• 107-05-1 3-chloroprop-1-ene 
• 220302-07-8 (Z)-3-bromo-1-iodopropene 
• 3066-75-9 allyl diethyl phosphate 
• 591-87-7 Allyl acetate 
• 35466-83-2 allyl methyl carbonate 
• 1730-25-2 allylmagnesium bromide 
• 7393-43-3 tetraallyl tin 
• 556-56-9 allyl iodid 

Relevant academic research and scientific papers

Merging metathesis and photochemical Csp3-H activation: Access to masked β-formyl hexanolides and their rearrangement to furofuranones

β-Masked formyl hexanolides were prepared by a three-step sequence including esterification of homoallylic alcohols, ring-closing metathesis and the photochemically induced addition of dioxanyl radical. When treated under oxidative conditions, the adducts underwent cleavage of the ketal group leading after rearrangement to parent furofuranones, structures found in some biological active compounds.

Generation of allyl Grignard reagents via titanocene-catalyzed activation of allyl halides

A protocol for the generation of allyl Grignard reagents via the catalytic activation of allyl halides is described herein. Subsequent nucleophilic addition to carbonyl derivatives provided the desired homo allylic alcohols in excellent yields (84-99%). E

Allylation of cyclohexanones in aqueous media and influence of facial amphiphilic fructopyranosides

The indium-catalyzed allylation reaction was performed in good yields and short reaction time with various cyclohexanones in water. Aqueous facial amphiphilic carbohydrates solutions were also screened for their potency to modify the stereochemical outcom

Organozinc generation via the titanium-catalyzed activation of alkyl halides

[Chemical Equation Presented] A protocol for the generation of organozinc reagents via catalytic activation of alkyl halides is described herein. Subsequent nucleophilic addition to carbonyl derivatives provided the desired products in good to excellent y

Reductive coupling of allylic esters with carbonyl compounds mediated by the mischmetall/[SmI2/Pd0cat.′] cat. system

The mischmetall/[SmI2/Pd0cat.′] cat. system has been used to mediate the allylation of ketones using a variety of allylic esters (acetates, carbonates and phosphates). Thus, a "two-stage catalysis" has been carried out using SmI2 and Pd(PPh3)4 in catalytic amounts together with mischmetall (an alloy of the light lanthanides) as a co-reductant. A catalytic scheme that takes into account previously reported reactions of SmI2/Pd 0cat. and mischmetall/SmI2,Cat. systems is proposed. It has also been shown that palladium complexes catalyse the addition of organolanthanide species to ketones. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

An efficient method for allylation of ketones with tetra-allylstannane

A variety of ketones undergo an allylation reaction with tetra-allyltin in the presence of a catalytic amount of Cu(OTf)2 or Sn(OTf)2. The method was found to be superior to most of the known methods, which are efficient only with al

Preparation of γ-heterosubstituted allylindium and diindium reagents and their reactions with carbonyl compounds

Various γ-heteroatom-substituted allylindium reagents were prepared, and their reactions with carbonyl compounds were examined. The reaction of 1,3-dibromopropene with metallic indium gave two types of organoindium species, γ-bromoallylindium and allylic

Zinc mediated allylation of aldehydes and ketones using allyl bromides and commercial zinc dust. the issue of regio- And stereoselectivity

An efficient procedure for the preparation of homoallylic alcohols has been achieved by a simple reaction of an aldehyde or a ketone with allyl bromide and commercial zinc dust in tetrahydrofuran. Excellent regioselectivity has been observed in the reaction of substituted allyl bromides.

Facile preparation of allylzinc species from allyl bromides and unactivated zinc induced by a catalytic amount of aluminum chloride and their reactions with carbonyl compounds and acetals

The effects of Lewis acids (ZnCl2, AlCl3, BF3, and TiCl4) on the generation of allylzinc species from allyl bromide and unactivated zinc powder in dry tetrahydrofuran (THF) were examined by trapping the organozinc compound with benzaldehyde, that is, Grignard-type allylation of the aldehyde. Among the Lewis acids employed, AlCl3 was found to be the promoter of choice. The allylzinc species preformed in the presence of a catalytic amount of AlCl3 effectively allylated carbonyl compounds. Various aromatic and aliphatic aldehydes as well as ketones were converted into homoallylic alcohols in good to excellent yields. Under the reaction conditions employed, ester, hydroxy, acetal, and aromatic nitro and halide groups were tolerated. In the case of α,β-unsaturated carbonyl compounds, selective 1,2-addition was observed. Substituted allyl bromides such as prenyl, crotyl, cinnamyl, and 2-cyclohexenyl bromides were smoothly converted to the corresponding allylzinc compounds, which reacted with carbonyl compounds to give substituted homoallylic alcohols in excellent yields. The diastereoselectivity in crotylation, cinnamylation, and 2-cyclohexenylation depended upon the structures of both the organic metals and the electrophiles. The origin of the observed selectivity is discussed. The allylation of dimethyl and cyclic acetals accompanied with carbon-oxygen bond cleavage also proceeded in excellent yields provided that two equivalents of AlCl3 was present.

Synthesis and reactivity of benzylic and allylic samarium compounds

Benzyl and allyl samarium species are prepared by reaction of benzylic or allylic chlorides with SmCp2. They present a wide scope of reactivity towards aldehydes, ketones and acid chlorides.