59417-89-9

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 2550-26-7 4-Phenyl-2-butanone 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 104-53-0 3-phenyl-propionaldehyde 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 97394-41-7 S-(4-nitrophenyl) 3-phenylpropanethioate 
• 31729-70-1 bis(iodozinc)methane 
• 7677-24-9 trimethylsilyl cyanide 
• 934-72-5 Methyl p-tolyl sulfoxide 
• 61157-31-1 3-phenylpropionyltrimethylsilane 
• 3112-85-4 methylphenylsulfonate 

Downstream Products

• 112712-27-3 5-hydroxy-6,6-dimethoxy-5-methyl-1-phenyl-3-hexanone 
• 137363-56-5 Thiocarbonic acid O-methyl ester S-(2-oxo-4-phenyl-butyl) ester 
• 121682-03-9 5-methoxy-1-phenylpentan-3-one 
• 20296-07-5 1-hydroxy-4-phenyl-2-butanone 
• 37985-17-4 1,4-diphenyl-2-butanone 
• 76837-21-3 2-methyl-4-oxo-6-phenyl-2-hexene 
• 93605-25-5 2-acetoxy-3-benzyl-4-oxo-1,4-dihydro-11bH-benzoquinolizine 
• 627106-93-8 C₁₃H₂₀O₂Si 
• 136068-05-8 1-(2-phenylethyl)cyclopropanol 

Relevant academic research and scientific papers

Iron- or silver-catalyzed oxidative fluorination of cyclopropanols for the synthesis of β-fluoroketones

The FeIII- or AgI-catalyzed oxidative fluorination of cyclopropanols via radical rearrangement is disclosed. This process features a straightforward and highly effective protocol for the site-specific synthesis of β-fluoroketones and represents an expedient method for the synthesis of γ-, δ- and ε-fluoroketones. Notably, this reaction proceeds at room temperature and tolerates a diverse array of cyclopropanols.

Iridium-catalyzed enantioselective allylation of silyl enol ethers derived from ketones and α,β-unsaturated ketones

The unified Ir-catalyzed enantioselective allylic substitution reactions of silyl enol ethers derived from ketones and α,β-unsaturated ketones with branched, racemic allylic alcohols are described. This transformation is catalyzed by the Carreira system and proceeds without fluoride, and with high ee and b:l ratio. The synthetic utility of this method was illustrated by the concise enantioselective total synthesis of marine natural products calyxolane A, B and by the assignment of the absolute configuration of calyxolane A.

Chemo- and regioselective preparation of zinc enolate from thiol esters by palladium catalyzed cross-coupling reaction

The palladium catalyzed cross-coupling reaction of thiol esters with bis(iodozincio)methane or 1,1-bis(iodozincio)ethane gave Reformatsky-type enolates. They can react with some electrophiles to give the corresponding adducts and were also trapped by silylation reagents to afford silyl enol ethers. As the method applicable to the thiol ester carrying ketone moiety, it afforded zinc enolates carrying ketone in the same molecule.

Reaction of acylsilanes with α-sulfinyl carbanions: Regioselective synthesis of silyl enol ethers

The reaction of acylsilanes with α-sulfinyl carbanions such as α-lithioalkyl sulfoxide is described. The reaction proceeds to give silyl enol ethers preferentially through the initial formation of the α-silyl alkoxide intermediates. In particular, the products derived from enolizable acylsilanes were the regio-defined silyl enol ethers that cannot be obtained by usual enolization of the corresponding unsymmetrical ketones with base.

Diastereoselective synthesis of five- and seven-membered rings by [2+2+1], [3+2], [3+2+2], and [4+3] carbocyclization reactions of β-substituted (alkenyl)(methoxy)carbene complexes with methyl ketone lithium enolates

β-Substituted alkenylcarbene complexes react with methyl ketone lithium etiolates to give different carbocyclization products depending on the structure of the lithium enolate, on the metal of the carbene complex, and on the reaction media. Thus, the reac

HISTONE DEACETYLASE INHIBITORS BASED ON ALPHACHALCOGENMETHYLCARBONYL COMPOUNDS

Histone deacetylase is a metallo-enzyme with zinc at the active site. Compounds having a zinc-binding moiety, for example, an alpha-chalcogenmethylcarbonyl group, such as an alpha-ketothio group, can inhibit histone deacetylase. Histone deacetylase inhibition can repress gene expression, including expression of genes related to tumor suppression. Accordingly, inhibition of histone deacetylase can provide an alternate route for treating cancer, hematological disorders, e.g., hemoglobinopathies, autosomal dominant disorders, e.g. spinal muscular atrophy and Huntington’s disease, genetic related metabolic disorders, e.g., cystic fibrosis and adrenoleukodystrophy, or for stimulating hematopoietic cells ex vivo.

A new method for the preparation of silyl enol ethers from carbonyl compounds and (trimenthylsily)diazomethane in a regiospecific and highly stereoselective manner

The reaction of lithium (trimethylsilyl)diazomethane with aldehydes and ketones has been investigated, and it has been found that quenching at low temperature with MeOH followed by addition of Rh2(OAc)4 gave silyl enol ethers in high yields. Quenching with other electrophiles (e.g., deuterium, MeI) gave terminal and substituted silyl enol ethers with complete control over regio- and stereochemistry. The mechanism of this novel process has been mapped out through a combination of deuterium labeling, ReactIR, and isolation of reaction intermediates. Copyright

Highly chemoselective rhodium-catalyzed methylenation of fluorine-containing ketones.

[reaction: see text] The rhodium(I)-catalyzed methylenation of functionalized fluorinated ketones using trimethylsilyldiazomethane proceeds to give the corresponding fluoromethylalkenes in good yields (61-90%). Remarkable chemoselectivity was observed for

Facile synthesis of silyl enol ethers by Mg-promoted coupling of aliphatic carbonyl compounds with trimethylsilyl chloride

Treatment of aliphatic carbonyl compounds with trimethylsilyl chloride with Mg turning for Grignard reaction without any pre-treatment in N,N- dimethylformamide at room temperature brought about highly facile, effective and stereoselective coupling to give the corresponding silyl enol ethers in good yields.

Regioselective synthesis of substituted (3E)-1,3-dienes from chelated allyl-ironcarbene complexes and potassium enoxyborates

The addition of potassium enoxyborates to the chelated allyl-ironcarbene complex 1 leads to the corresponding η-(3E)-1,3-diene complexes 2 in fair yields. Complexes 2 can be demetalated with ceric ammonium nitrate (CAN) to give unrearranged (3E)-6-oxo-1.3-dienes 3. Prior to decomplexation, the carbonyl group can be further modified. This is demonstrated by the syntheses of the natural terpene alcohol hotrienol and of a complexed methylene- separated dienyne. Potassium enoxyborates are superior to lithium enolates as they are readily prepared in situ from a variety of aldehydes and ketones which do not form sufficiently stable lithium derivatives. In contrast to lithium enolates, only C- C coupling products derived from the 'kinetic' regioisomers are formed from unsymmetrical aliphatic ketones.