180295-26-5

Upstream product

• 53172-91-1 (benzyloxy)(tert-butyl)dimethylsilane 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 132868-67-8 (tert-butyldimethylsilyl)(phenyl)methanone 
• 100-52-7 benzaldehyde 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 451-40-1 phenyl benzyl ketone 

Downstream Products

• 132161-98-9 2-t-butyldimethylsilyloxy-1,2-diphenyl ethanol 
• 134-81-6 benzil 
• 5496-33-3 2-(4-bromophenyl)-4,5-diphenyl-1H-imidazole 
• 63859-84-7 3-methyl-4,5-diphenyl-2(5H)-furanone 
• 877869-66-4 (Z)-methyl 4-(tert-butyldimethylsiloxy)-2-methyl-3,4-diphenyl-2-butenoate 
• 188924-49-4 [2-(tert-Butyl-dimethyl-silanyloxy)-1,2-diphenyl-ethoxycarbonylamino]-acetic acid methyl ester 
• 188924-51-8 (4-Hydroxy-2-oxo-4,5-diphenyl-oxazolidin-3-yl)-acetic acid methyl ester 
• 188924-50-7 (2-Hydroxy-1,2-diphenyl-ethoxycarbonylamino)-acetic acid methyl ester 
• 371158-05-3 1,2-diphenylbut-3-yne-1,2-diol 
• 1084-78-2 (1RS,2SR)-(+/-)-1,2-diphenyl-1,2-propandiol 
• 1084-78-2 (1RS,2RS)-(+/-)-1,2-diphenyl-1,2-propandiol 

Relevant academic research and scientific papers

N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes

We found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce aryl alkyl ketones. The mild and transition-metal-free reaction conditions are attractive features of this method. The power of this protocol was demonstrated by the functionalization of pharmaceutical drugs and natural product. A reaction pathway involving single electron transfer from an enolate form of Breslow intermediate to a redox ester followed by recombination of the resultant radical pair to form a carbon-carbon bond is proposed.

Catalytic oxidation of silyl enol ethers to 1,2-diketones employing nitroxyl radicals

A novel and efficient method for the preparation of 1,2-diketones is reported. A series of -diketones were readily prepared by the nitroxyl-radical-catalyzed oxidation of silyl enol ethers using magnesium monoperoxyphthalate hexahydrate (MMPP6H) as the co-oxidant. Georg Thieme Verlag Stuttgart · New York.

Mechanism and scope of the cyanide-catalyzed cross silyl benzoin reaction

In this work, cross silyl benzoin addition reactions between acylsilanes (1) and aldehydes (2) catalyzed by metal cyanides are described. Unsymmetrical aryl-, heteroaryl-, and alkyl-substituted benzoin adducts can be generated in moderate to excellent yie

Substituted imidazoles as glucagon receptor antagonists

A modestly active, nonselective triarylimidazole lead was optimized for binding affinity with the human glucagon receptor. This led to the identification of a 2- and/or 4-alkyl or alkyloxy substituent on the imidazole C4-aryl group as a structural determinant for significant enhancement in binding with the glucagon receptor (e.g., 41, IC50 = 0.053 μM) and selectivity (> 1000 ×) over p38 MAP kinase in this class of compounds.

Efficient and chemoselective protection of alcohols and phenols with tert-butyldimethylchlorosilane (TBDMCS) under solvent-free conditions

Various types of primary and secondary alcohols and phenols can be converted efficiently to their corresponding TBDMS ethers using TBDMCS/imidazole under solvent-free conditions. Elimination of DMF, accompanied with an easy non-aqueous work-up and a high rate enhancement of the reaction are worthy to be mentioned for the presented method. The reactions show absolute chemoselectivity for the protection of primary in the presence of secondary alcohols.

Synthesis and properties of carbamoyl derivatives of photolabile benzoins

Carbamoyl derivatives of photolabile benzoins, particularly of 3',5'-dimethoxybenzoin, are readily prepared via the mixed p-nitrophenyl carbonate of the benzoin. The method is most suitable for secondary amines, since many primary amines exist in varying proportions as the cyclic In alkaline solution (0.2 M NaOH) the carbamates of unsymmetrical benzoins are readily equilibrated. Flash photolysis of 3',5'-dimethoxybenzoin carbamates generates the carbamate anion in a fast heterolytic process and liberation of the amine is controlled by the rate of decarboxylation.

Diastereomerically Pure 3-(Silyloxy)oxetanes by a Selective Paterno-Buechi Reaction

Diastereomerically pure 3-oxetanes 3 were prepared in moderate to good yields (45-72percent) by the Paterno-Buechi reaction of silyl enol ethers 2 with benzaldehyde.The phorocycloaddition exhibits a high degree of regio- and diastereoselectivity.The substituents R in the silyl enol ether have been varied , and it was found that steric bulk is mainly responsible for enhanced selectivity (diastereoselectivity from 70:30 up to 95:5).The regiochemical control is perfect (regioselectivity > 95:5) except for silyl enol ether 2a (R = Me) in the case of which a 90:10 ratio of regioisomers was observed.Irradiation of the reaction mixture at lower temperature (-25 deg C) led to a further improvement of diastereoselectivity.The relative configuration of the products obtained was elucidated both by 1H-NMR spectroscopy and by chemical degradation.As a mechanistic hypothesis to explain the high observed diastereoselectivity we propose that the steric environment in the intermediate diradical 11 determines the stereoselectivity according to two possible reaction pathways, i.e. bond formation and retrocleavage. - Key Words: Paterno-Buechi reaction / Oxetanes / Diastereoselectivity / Enol silyl ethers / Photocycloaddition