56583-95-0

Upstream product

• 58309-61-8 dimethyl(2-methyl-1,3-dithiacyclohexan-2-yl)phenylsilan 
• 79-20-9 acetic acid methyl ester 
• 3839-31-4 dimethyl(phenyl)silyllithium 
• 127-19-5 N,N-dimethyl acetamide 
• 79678-02-7 (1-methoxyvinyl)dimethyl(phenyl)silane 
• 107-25-5 methoxyethene 
• 768-33-2 phenyldimethylsilyl chloride 
• 1696-20-4 4-acetylmorpholine 
• 176646-58-5 1-(dimethylphenylsilyl)-1-ethoxyethene 
• 109-92-2 ethyl vinyl ether 
• 505-23-7 1,3 dithiane 
• 5830-31-9 N,N-dimethyl-3-phenylpropanamide 
• 130255-51-5 1,1-bisethanol 

Downstream Products

• 98-85-1 1-Phenylethanol 
• 5272-18-4 dimethylphenylsilanol 
• 56-33-7 1,1,3,3-tetramethyl-1,3-diphenyldisiloxane 
• 193006-90-5 ethyl (Z)-3-(dimethyl(phenyl)silyl)-2-butenoate 
• 193006-89-2 ethyl (E)-3-(dimethyl(phenyl)silyl)-2-butenoate 
• 91025-67-1 2-methyl-1,3,5-triphenyl-1H-pyrrole 
• 56138-25-1 2-methyl-3,5-diphenyl furan 
• 889130-08-9 ethyl (R)-3-(dimethylphenylsilyl)butanoate 
• 205752-81-4 ethyl (S)-3-(dimethyl(phenyl)silyl)butanoate 

Relevant academic research and scientific papers

Regio- and Stereoselective Synthesis of Fully Substituted Silyl Enol Ethers of Ketones and Aldehydes in Acyclic Systems

The regio- and stereoselective preparation of fully substituted and stereodefined silyl enol ethers of ketones and aldehydes through an allyl-Brook rearrangement is reported. This fast and efficient method proceeds from a mixture of E and Z isomers of easily accessible starting materials.

Iridium-Catalyzed Enantioselective Hydrogenation of Vinylsilanes

We have screened a diverse array of iridium complexes derived from chiral N,P ligands as catalysts for the asymmetric hydrogenation of vinylsilanes, a transformation for which generally applicable catalysts were lacking. Several catalysts emerged from thi

Enantioselective synthesis of allylsilanes bearing tertiary and quaternary si-substituted carbons through Cu-catalyzed allylic alkylations with alkylzinc and arylzinc reagents

All sorts of allylsilanes including, for the first time, those that contain a Si-bonded quaternary carbon, were synthesized through efficient and highly enantioselective Cu-catalyzed asymmetric allylic alkylations. Reactions may involve dialkyl- as well as diarylzinc reagents and are promoted by various chiral N-heterocyclic carbene complexes.

Chiral silanes via asymmetric hydrosilylation with catalytic CuH

CuH-catalyzed asymmetric conjugate reduction of β-silyl-α, β-unsaturated esters has been developed. Using PMHS as a stoichiometric source of hydride and in situ generated CuH ligated by Solvias' JOSIPHOS analogue PPF-P(t-Bu)2 leads to highly enantioselective 1,4-reductions.

Efficient synthesis of acylsilanes using morpholine amides

(Chemical Equation Presented) A general synthesis of acylsilanes from the corresponding morpholine amides and silyllithium species is described. The use of morpholine amides is economical and prevents over-addition by the silyl nucleophile. The procedure cleanly affords acylsilanes in good yields and circumvents the use of stoichiometric copper(I) cyanide typically employed to synthesize these compounds from acid chlorides.

The extraordinary reactions of phenyldimethylsilyllithium with N,N-disubstituted amides

The reactions of the silyllithium reagent with tertiary amides was discussed. The enediamines were easily isomerized from cis to trans, easily oxidized to dienediamines and were hydrolyzed to α-aminoketones. If the two equivalents of the silyllithium reagent were used, the product was an α-silylamine. The results show that each member of the homologous series of amides gives rise to a substantially different product.

Formation of α-dialkylamino alkyllithium intermediates in the reaction of N,N-dialkylamides with PhMe2SiLi followed by a second lithium reagent, and their alkylation, fragmentation, cyclisation and rearrangement by proton transfer

Tertiary amides (RCONMe2) react with PhMe2SiLi, followed by a second lithium reagent NuLi, to give α-dialkylamino alkyllithium intermediates R(Me2N)CLiNu that undergo protonation 2 → 3, alkylation 2a → 3ab, β-elimination 5 → 6, intramolecular attack on an isolated double bond 9 → 10, intramolecular proton transfer 12, 17 and 22 (arrows), and fragmentation 28 and 34 (arrows), depending upon the structures of the various components R and Nu.

Highly stereoselective syntheses of alkenylsilanes and germanes utilizing cyclobutyl ketones

(E)-Alkenylsilanes were synthesized with high stereoselectivity by the diastereoselective addition of the dimethylphenylsilyllithium to the trans-2-phenylthiocyclobutyl ketones and the Lewis acid-promoted promoted stereospecific ring opening reactions of the resulting cyclobutanemethanol derivatives. (E)-1,5-Disubstituted 1,5-dienylsilanes and germanes were also produced stereoselectively by the similar zinc salt-catalyzed ring opening reaction of α-dimethylphenylsilyl- or α-triethylgermyl-1-[2-(trimethylsilylmethyl)cyclobutane]methanol derivatives.

Synthesis of Acylsilanes from Amides and Esters, and the Selective Oxidation of α-Silyl Alcohols to Aldehydes

The acylsilanes 2 can easily be made directly from the dimethylamides 3 by treatment with phenyldimethylsilyllithium.They can also be made in two steps from the esters 4 using 2 equiv. of phenyldimethylsilyllithium followed by oxidation of the disilyl alcohols 5 with PDC.The disilyl alcohols 5 can be used as intermediates in the conversion of esters into aldehydes without recourse to hydride reagents, by monodesilylation, using a Brook rearrangement, followed by oxidation and selective removal of the silyl group, using chromium trioxide in DMSO.

Synthesis of acetyldimethyl(phenyl)silane and its enantioselective conversion into (R)-(1-hydroxyethyl)dimethyl(phenyl)silane by plant cell suspension cultures of Symphytum officinale L. and Ruta graveolens L.

Starting from chlorodimethyl(phenyl)silane (3), acetyldimethyl(phenyl)silane (1) was prepared by a two-step synthesis in a total yield of 90percent PhMe2SiC(OMe)=CH2 (4) PhMe2SiC(O)Me (1)>.The prochiral acetylsilane 1 was transformed enantioselectively into (R)-(1-hydroxyethyl)dimethyl(phenyl)silane using plant cell suspension cultures of Symphytum officinale L. or Ruta graveolens L.Under preparative conditions (300-mg scale, not optimized), (R)-2 was isolated in 15percent (Symphytum) and 9percent yield (Ruta), respectively.The enantiomeric purities of the products were 81percent ee (Symphytum) and 60percent ee (Ruta), respectively.