27575-61-7

Upstream product

• 67845-50-5 8-hydroxy-2,6-dimethyl-nona-2,6-diene 
• 81535-53-7 (Z)-methyl-4-(4-methyl-3-pentenyl)but-3-en-2-ol 
• 106-25-2 Nerol 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 106-26-3 cis-3,7-dimethyl-2,6-octadienal 

Downstream Products

• 802621-96-1 (2Z-3,7-dimethyl-1-methyleneocta-2,6-dieneyloxy)triisopropylsilane 
• 802622-17-9 4-hydroxymethyl-3-methyl-3-(4-methylpent-3-enyl)cyclohexanone 
• 3664-64-0 rac-4,8-dimethyl-7-nonen-2-one 
• 144428-81-9 2-hydroxy-6-acetyl-1,2,5-trimethylcyclohexane 
• 144428-84-2 4-hydroxy-2-acetyl-1,1,3-trimethylcyclohexane 
• 27539-94-2 (3E)-4,8-dimethylnona-3,7-dien-2-one 
• 37709-66-3 2,6,6-trimethyl-2-cyclohexenyl methyl ketone 

Relevant academic research and scientific papers

Copper-Catalyzed One-Pot Borylative Aldolisation β-Fluoride Elimination for the Formal Addition of Acrylates to Carbonyl Moieties

Herein, we report the copper-catalyzed domino borylation/aldolisation of methyl 2-fluoroacrylate with carbonyl compounds followed by an elimination to give Morita–Baylis–Hillman (MBH) analogues. The optimal conditions described were shown to be compatible

Allylic substitution for construction of a chiral quaternary carbon possessing an aryl group

Phenylcopper reagents derived from 2:1 PhMgBr/Cu(acac)2 and 3:1:1 PhMgBr/Cu(acac)2/ZnI2 were found to be highly reactive and regioselective in the allylic substitution of γ,γ- disubstituted secondary allylic picolinates designed for construction of a quaternary carbon, whereas the previous 2:1 ArMgBr/CuBr·Me2S reagent and that with ZnX2 were unsuccessful. The generality of the ArMgBr/Cu(acac)2 reagent was examined with enantiomerically enriched allylic picolinates, which furnished quaternary carbons with high efficiency in >92% regioselectivity and >97% chirality transfer. Two cyclohexanes with a quaternary carbon were synthesized by using these reagents.

The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.

Challenge toward structural complexity using asymmetric catalysis: Target-oriented development of catalytic enantioselective Diels-Alder reaction

(Chemical Equation Presented) A new method for the catalytic enantioselective Diels-Alder reaction using polysubstituted silyl enol ethers as dienes is described. High enantioselectivity (up to 92% ee) was produced using a catalyst generated from FeBr3 and AgSbF6 in a 1:2 ratio and aryl-pybox (aryl = Ph or p-ethoxyphenyl). This reaction should facilitate the enantioselective synthesis of polycyclic acylphloroglucinols such as hyperforin or garsubellin A, which are currently of interest from synthetic and medicinal points of view.

PHOTOCHEMISCHE REAKTIONEN

On 1n,?*-excitation (λ>347 nm) citral (5) and the methyl ketone 10 isomerize to compounds A (7, 19) and B(6, 20), whereas the phenyl ketone 11 changes into the isomer 24 of type E. evidence is given that the conversion to A and B may arise from the 3n,?*-state of the 2,6-diene-carbonyl compounds.On 1p,?*-excitation (λ=254 nm) 5 and 10 yield the isomers A (7, 19) and D (18, 22), but no products of type B.Futhermore, conversion of 10 to the isomer 21 of type C is observed.Selective 1?,?*-excitation (λ=254 nm) as well as selective 1n,?*-excitation (λ>347 nm) of the 2,7-diene-carbonyl compounds 12 and 13 give rise to isomerization to the compounds F (25, 28), exclusively.The intramolecular (2+2)-photocycloadditions are shown to be triplet processes.UV.-irradiation (λ>280 nm) of compounds F (25, 28) furnishes the isomeric products G (26, 29) which photoisomerize to oxetanes of type H (27, 30).