862735-92-0

Upstream product

• 6089-04-9 3-(tetrahydropyran-2'-yloxy)propyne 
• 768-33-2 phenyldimethylsilyl chloride 
• 110-87-2 3,4-dihydro-2H-pyran 

Downstream Products

• 126361-99-7 (Z)-3-(dimethyl-phenyl-silanyl)-prop-2-en-1-ol 
• 862735-81-7 dimethyl-phenyl-[(Z)-3-(tetrahydro-pyran-2-yloxy)-propenyl]-silane 
• 126361-64-6 cis-1-Dimethylphenylsilyl-2-vinylcyclopropane 
• 130485-31-3 r-1-Dimethylphenylsilyl-c-2-formyl-c-3-methylcyclopropane 
• 130485-28-8 cis-1-Dimethylphenylsilyl-2-hydroxymethylcyclopropane 
• 130485-30-2 r-1-Dimethylphenylsilyl-t-2-hydroxymethyl-c,t-3-methylcyclopropane 
• 126361-67-9 (Z)-5-Dimethylphenylsilyl-1-phenylthio-2-pentene 
• 130485-54-0 (Z)-5-Dimethylphenylsilyl-5-iodo-1-tridecafluorohexyl-2-pentene 
• 130485-53-9 (E)-5-Dimethylphenylsilyl-5-iodo-1-tridecafluorohexyl-2-pentene 
• 1407797-83-4 (R)-6-(dimethylphenylsilyl)-7-octen-1-yl pivalate 
• 1407797-72-1 (Z)-1-dimethylphenysilyl-3-chloro-1-pentene 
• 1407797-81-2 (R)-dimethylphenyl(1-undecen-3-yl)silane 
• 1407797-91-4 C₁₉H₃₄Si 
• 1407797-82-3 (R)-[8-(1,3-dioxan-2-yl)-1-octen-3-yl]dimethylphenylsilane 

Relevant academic research and scientific papers

Ni-catalyzed direct carboxylation of propargylic alcohols with carbon dioxide

The carboxylation of propargylic alcohols containing a silyl group at the terminal position was conducted in a CO2 atmosphere at atmospheric pressure in the presence of a nickel catalyst and diethylzinc. Here, CO2 was used as not only the C1 source but also the promoter of the COH cleavage processes for the oxidative addition of propargylic alcohols.

Direct Access to Allenylphosphine Oxides via a Metal Free Coupling of Propargylic Substrates with P(O)H Compounds

A direct and convenient approach for the coupling of propargylic substrates with diphenylphosphine oxide in the presence of Tf2O and 2,6-lutidine has been developed. The method provides a general approach for the construction of attractive allenylphosphoryl skeletons with high atom and step economy under metal free conditions.

Access to Stereodefined (E)-2-Silylallylboronates via Regioselective Chloroboration of Allenylsilanes

A catalyst-free method for the highly regioselective chloroboration of allenylsilanes is described. In the presence of BCl3 and 2,6-lutidine, chloroboration of allenylsilanes proceeds smoothly without any catalyst, and the product could be treated with pinacol to afford the corresponding pinacol borates in one-pot reaction. This reaction provides a direct approach to construct valuable 2-silylallylboronate frameworks with operational simplicity and high atom-economy.

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

Synthesis and Isolation of Organogold Complexes through a Controlled 1,2-Silyl Migration

During our efforts toward the synthesis of naturally occurring polyprenylated polycyclic acylphloroglucinol using a AuI-catalyzed 6-endo dig carbocyclization, we isolated stable vinyllic gold intermediates. Optimization lead to isolated yields of up to 98 %, using 2-(di-tert-butylphosphino)biphenyl as the ligand. This transformation is derived from a silyl rearrangement that can be fully controlled according to the nature of the substituent on the ynone. This selective transformation does not require basic conditions to prevent protodeauration. These vinylgold complexes are the first isolated intermediates during a silyl migration with gold(I). More than 16 new organogold complexes were synthesized and characterized by single-crystal X-ray diffraction. Reactivity of these complexes is also presented.

Copper-catalyzed enantioselective allylic substitution with alkylboranes

The first catalytic enantioselective allylic substitution reaction with alkylboron compounds has been achieved. The reaction between alkyl-9-BBN reagents and primary allylic chlorides proceeded with excellent γ-selectivities and high enantioselectivities under catalysis of a Cu(I)-DTBM-SEGPHOS system. The protocol produces terminal alkenes with an allylic stereogenic center branched with functionalized sp3-alkyl groups. The reaction with a γ-silicon-substituted allyl chloride affords an efficient strategy for the enantioselective synthesis of functionalized α-stereogenic chiral allylsilanes.

Stereoselective synthesis of E,Z-configured 1,3-dienes by ring-closing metathesis. Application to the total synthesis of lactimidomycin

Strategic positioning of a silyl group on the diene unit of a diene-ene substrate allows rigorous regio- and stereocontrol to be exerted during metathesis-based macrocyclization reactions. The versatility of this concise approach to E,Z-configured 1,3-die

A convenient multigram synthesis of highly enantioenriched methyl 3-silylglycidates

A multigram scale synthesis of the four stereoisomers of methyl 3-silylglycidates (epoxysilanes) with high enantiopurity is described. Key reactions include a Sharpless asymmetric epoxidation (SAE) of a trans-vinylsilane and an enzymatic resolution of a r

Synthesis and [4 + 2]-annulation of enantioenriched (Z)-crotylsilanes: Preparation of the C1-C13 fragment of bistramide A

(Chemical Equation Presented) New chiral crotylsilanes that bear a (Z)-olefin geometry were synthesized in high enantiopurity. The reagents participate in [4 + 2]-annulations with aldehydes to give stereochemically complementary pyrans (relative to (E)-crotylsilanes) bearing 2,6-cis-5,6-cis and 2,6-trans-5,6-cis relationships of peripheral functionalities. A stereoselective synthesis of the C1-C13 fragment of bistramide A is also described highlighting this annulation strategy.

A route to enantiomerically-enriched α-silyl aldehydes from 2,3-epoxy alcohols

Asymmetric epoxidation of (E)-3-trialkylsilyl-2-propen-1-ols gives the expected epoxides with high enantioselectivity. Ring opening reactions of these epoxides with organocopper reagents furnishes 1,2-diols which are readily cleaved with Pb(OAc)4 to afford α-silyl aldehydes with no detectable loss of stereochemistry.