41608-14-4

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 563-79-1 2,3-Dimethyl-2-butene 
• 93-89-0 benzoic acid ethyl ester 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 3017-70-7 2-bromo-3-methylbut-2-ene 
• 98-86-2 acetophenone 
• 797802-44-9 1-tert-butyl-2-phenylcyclopropane 
• 563-80-4 3-methyl-butan-2-one 
• 100-52-7 benzaldehyde 
• 5072-70-8 1-bromo-2,3-dimethyl-2-butene 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 

Relevant academic research and scientific papers

PhI(OAc)2-mediated alkoxyoxygenation of β,γ-unsaturated ketoximes: Preparation of isoxazolines bearing two contiguous tetrasubstituted carbons

A PhI(OAc)2-promoted dioxygenation of allyl oximes, including one alkoxylation, has been developed. This reaction can give isoxazoline products bearing two contiguous tetrasubstituted carbons. Various oximes substrates bearing different aryl groups and tetrasubstituted-olefin moieties were compatible with the mild reaction conditions. A two-electron oxidation pathway was proposed based on results of preliminary mechanistic studies.

Asymmetric Aza-Wacker-Type Cyclization of N-Ts Hydrazine-Tethered Tetrasubstituted Olefins: Synthesis of Pyrazolines Bearing One Quaternary or Two Vicinal Stereocenters

We have developed an asymmetric aza-Wacker-type cyclization of N-Ts hydrazine-tethered tetrasubstituted olefins, affording optically active pyrazolines bearing chiral tetrasubstituted carbon stereocenters. This reaction is tolerant to a broad range of substrates under mild reaction conditions, giving the desired chiral products with high enantioselectivities. Generation of two vicinal stereocenters on the C=C double bonds was also achieved with high selectivities, a process which has been rarely studied for Wacker-type reactions. A mechanistic study revealed that this aza-Wacker-type cyclization undergoes a syn-aminopalladation process. It was also found that for substrates bearing two linear alkyl substituents on the outer carbon atom of the olefin, both of which are larger than a methyl group, the alkyl substituent that is cis to the intranucleophilic group participates more readily in β-hydride elimination. When one of the two alkyl substituents on the outer carbon atom of the olefin is a methyl group, β-hydride elimination proceeds selectively at the methylene side, thus both diastereomers can be prepared via switching the configuration of the olefin. Furthermore, the product can be converted to a pharmaceutical compound in high yields over three steps.

One-Pot Synthesis of β,β-Disubstituted α,β-Unsaturated Carbonyl Compounds

TiCl4-promoted aldol reaction of ketones as aldol acceptors followed by elimination of the titanoxy group from the Ti-aldolates affords β,β-disubstituted α,β-unsaturated carbonyl compounds in a one-pot procedure. The use of additives, such as DMF, N,N,N′,N′-tetramethylethylenediamine, and pyridine, in the elimination step was found to be important.

New aspects of nitrosation of arylcyclopropanes: Nitrosation of phenylcyclopropanes with bulky alkyl substituents in the small ring

It has been shown for the first time that nitrosation of phenylcyclopropanes with bulky alkyl substituents in the small ring proceeds predominantly with attack of the nitrosonium cation on the benzyl carbon atom of the cyclopropane ring with intermediate

Palladium-catalyzed α-vinylation of carbonyl compounds

A mild, general, catalytic system for the α-vinylation of carbonyl compounds has been developed. By employing [Pd(P1Bu 3)Br]2 as catalyst and LHMDS as base, vinyl bromides, vinyl triflates, and vinyl tosylates couple with 3-methyioxindole in satisfactory yields. The same catalytic system is extended to the α-vinylation of ketones and esters.

Reactions of substituted (2-butene-1,4-diyl)magnesium complexes with carboxylic esters and lactones: Formation of a versatile intermediate capable of generating substituted cyclopentenols, fused-ring cyclopentenols, or β,γ-unsaturated ketones

Reaction of the magnesium complexes of substituted 1,3-dienes with either carboxylic esters or lactones at low temperature (-78 to -10°C) generates the magnesium salt of a cyclopropanol. This intermediate can either be trapped as an acetate of the cyclopr

Photochemical Reactions of Arenecarboxylic Acid Esters with Electron-Rich Alkenes: 2 + 2 Cycloaddition, Hydrogen Abstraction, and Cycloreversion

The photochemical reaction of arenecarboxylic acid methyl esters and isopropyl esters with alkenes has been examined and found to afford three types of products: (a) 2-alkoxyoxetanes 3 via a direct 2 + 2 cycloaddition to the substrate alkenes; (b) β,γ-unsaturated ketones 5 via hydrogen abstraction by the carbonyl oxygen of the photoexcited ester from an allylic position of the substrate alkene; and (c) alkoxyalkenes 4, which arise via 2 + 2 cycloreversion of the oxetanes 3.The quantum yields for the formation of the various products generally fell in the range 0.005-0.03, approximately 1 order of magnitude less than those of aryl ketones and aldehydes undergoing similar reactions.