103223-44-5

Upstream product

• 103223-43-4 3,4-Bis-2-butenyl acetate 
• 74-85-1 ethene 
• 17156-64-8 (dimethylphenylsilyl)acetylene 
• 768-33-2 phenyldimethylsilyl chloride 
• 126-99-8 chloroprene 
• 3839-31-4 dimethyl(phenyl)silyllithium 

Downstream Products

• 103223-45-6 4-Dimethylphenylsilyl-1,2,3,6-tetrahydrophthalic anhydride 
• 1187817-03-3 (E)-dimethyl(phenyl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-ene-2-yl)silane 
• 1187817-15-7 (E)-dimethyl(phenyl)(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-en-2-yl)silane 
• 1307279-32-8 3-(dimethyl(phenyl)silyl)-3-vinylisochroman-1-one 
• 1310886-85-1 (1R,2R)-1-(benzo[d][1,3]dioxol-5-yl)-3-(dimethyl(phenyl)silyl)-2-methylbut-3-en-1-ol 
• 1310886-93-1 (3R,4S)-2-(dimethyl(phenyl)silyl)-3-methyldec-1-en-4-ol 
• 1310886-91-9 (3R,4S,Z)-2-(dimethyl(phenyl)silyl)-3,6,10-trimethylundeca-1,5,9-trien-4-ol 
• 1310886-88-4 (3R,4S,E)-2-(dimethyl(phenyl)silyl)-3,6,10-trimethylundeca-1,5,9-trien-4-ol 
• 1310886-87-3 (3R,4S)-2-(dimethyl(phenyl)silyl)-3,6-dimethylhepta-1,5-dien-4-ol 
• 1310886-86-2 (3R,4R,E)-5-(dimethyl(phenyl)silyl)-2,4-dimethyl-1-phenylhexa-1,5-dien-3-ol 
• 1310886-95-3 (3R,4S)-7-(benzyloxy)-2-(dimethyl(phenyl)silyl)-3-methylhept-1-en-4-ol 
• 1310886-83-9 (1R,2R)-3-(dimethyl(phenyl)silyl)-1-(2-methoxyphenyl)-2-methylbut-3-en-1-ol 
• 1310887-00-3 tert-butyl((3-(dimethyl(phenyl)silyl)-2-methyl-1-phenylbut-3-en-1-yl)oxy)dimethylsilane 
• 1310886-78-2 (1R,2R)-3-(dimethyl(phenyl)silyl)-2-methyl-1-phenylbut-3-en-1-ol 

Relevant academic research and scientific papers

Stereochemical Characterization of Polyketide Stereotriads Synthesized via Hydrogen-Mediated Asymmetric syn-Crotylation

The stereoselective access to stereotriads as important polyketide building blocks is reported on the basis of the Krische-type hydrogen-mediated syn-crotylation. The products were obtained with an extremely high diastereoselectivity (dr >99:1), and the n

Syntheses of 2-silicon-substituted 1,3-dienes

A number of 2-silicon substituted 1,3-dienes have been prepared by one of three routes: 1) Reactions of 1,3-dienyl Grignard reagents with silyl electrophiles or silyl Grignard reagents with 1,3-dienyl electrophiles; 2) Hydrosilylation of enynes; 3) Enyne cross metathesis. The strengths and limitations of each preparative method are discussed.

Diastereo- and enantioselective ruthenium-catalyzed hydrohydroxyalkylation of 2-silyl-butadienes: Carbonyl syn -crotylation from the alcohol oxidation level

Exposure of alcohols 2a-2j to 2-silyl-butadienes in the presence of ruthenium complexes modified by (R)-SEGPHOS or (R)-DM-SEGPHOS results in redox-triggered generation of allylruthenium-aldehyde pairs, which combine to form products of carbonyl crotylation 4a-4j in the absence of stoichiometric byproducts and with high levels of syn-diastereo- and enantioselectivity. In the presence of isopropanol under otherwise identical conditions, aldehydes 3a-3j are converted to an equivalent set of adducts 4a-4j. Whereas reactions conducted using conventional heating require 48 h, microwave irradiation enables full conversion in only 4 h. Finally, as illustrated in the conversion of adduct 4a to compounds 6a and 6b, diastereoselective hydroboration-Suzuki cross-coupling with aryl and vinyl halides followed by Fleming-Tamao oxidation enables generation of anti,syn-stereotriads found in numerous polyketide natural products.

A strategy for the synthesis of well-defined iron catalysts and application to regioselective diene hydrosilylation

We report the development of a well-defined Fe catalyst and its application to the regio-and stereoselective 1,4-hydrosilylation of 1,3-dienes. To the best of our knowledge, this is the first example of accessing a characterized low-valent Fe catalyst by controlled reductive elimination from a readily accessible Fe precatalyst.

Preparation of 2-silicon-substituted 1,3-dienes and their diels-alder/cross-coupling reactions

(Chemical Equation Presented) 2-Triethoxysilyl-substituted 1,3-butadiene has been prepared in 30-g quantities from chloroprene via a simple synthetic procedure. Silatrane- and catechol-substituted analogues of this main group element substituted diene wer

Iron-catalyzed 1,4-hydroboration of 1,3-dienes

(Chemical Equation Presented) A chemo-, regio-, and stereoselective iron-catalyzed 1,4-hydroboration of dienes that affords γ-disubstituted allylboranes has been developed. 1,4-Hydroboration of 2-substituted dienes forms allylborane products with (E)-trisubstituted double bonds exclusively.

COMPOUNDS AND COMPOSITIONS CONTAINING SILICON AND/OR OTHER HETEROATOMS AND/OR METALS AND METHODS OF MAKING AND USING THEM

The present invention relates to compounds, intermediates, compositions, and methods of making compounds and intermediates related to the compounds of Formula (I) and/or Formula (II) and/or Formula (III) and/or Formula (IV) and/or Formula (VI) and/or Formula (VII) as disclosed herein wherein the various substituents are as defined in the written description.

Cationic rearrangements controlled by the presence of a silyl group

1,1-Disilylcarbinols having two alkyl groups on the adjacent carbon atom react with thionyl chloride in sulfur dioxide to give the product in which one of the alkyl groups has migrated towards the two silyl groups, and one of the silyl groups has been removed from the resultant cation. The reaction is seen in ring-expansion, as in the conversion of cyclohexylbis[dimethyl(phenyl)silyl]carbinol (7) into 1-dimethyl(phenyl) silylcycloheptene (11), and in open chains, as in the conversion of 1,1-bis[dimethyl(phenyl)silyl]-2-methylpropanol (26) into (E)- and (Z)-2-dimethyl(phenyl)silylbut-2-ene (27). Phenyldimethylsilyllithium reacts with pinacolone to give the α-silyl carbinol (44), which rearranges in the same way to give 2,3-dimethylbut-2-ene (46), effectively achieving a pinacolone-to-pinacol rearrangement.

Simple Syntheses of 2-Silyl- and 2-Stannyl-1,3-butadienes

2-Dimethylphenylsilylbutadiene and 2-tributylstannylbutadiene are prepared from 2-butyne-1,4-diol.