205752-75-6

Upstream product

• 205752-97-2 1,3-bis[dimethyl(phenyl)silyl]butyne 
• 215546-22-8 3-(dimethylphenylsilyl)-1-(trimethylsilyl)but-1-yne 
• 146758-90-9 1-dimethyl(phenyl)silylbut-1-yne 
• 768-33-2 phenyldimethylsilyl chloride 

Downstream Products

• 215546-29-5 1-Cyclohexyl-4-(dimethyl-phenyl-silanyl)-pent-2-yn-1-ol 
• 215546-03-5 Acetic acid (E)-1-cyclohexyl-4-(dimethyl-phenyl-silanyl)-pent-2-enyl ester 
• 215546-34-2 (E)-1-Cyclohexyl-4-(dimethyl-phenyl-silanyl)-pent-2-en-1-ol 
• 132841-67-9 Toluene-4-sulfonic acid (1R,4R)-1-cyclohexyl-4-(dimethyl-phenyl-silanyl)-pentyl ester 
• 132841-67-9 Toluene-4-sulfonic acid (1S,4R)-1-cyclohexyl-4-(dimethyl-phenyl-silanyl)-pentyl ester 
• 132841-63-5 (Z)-(1S,4R)-1-Cyclohexyl-4-(dimethyl-phenyl-silanyl)-pent-2-en-1-ol 
• 132841-63-5 (Z)-(1R,4R)-1-Cyclohexyl-4-(dimethyl-phenyl-silanyl)-pent-2-en-1-ol 
• 679410-10-7 {Dimethyl-[(E)-1-methyl-4-(1-trimethylsilanyloxy-vinyloxy)-but-2-enyl]-silanyl}-benzene 
• 679409-99-5 (E)-4-dimethyl(phenyl)silylpent-2-enyl acetate 
• 679410-20-9 (E)-4-dimethyl(phenyl)silylpent-2-en-1-ol 

Relevant academic research and scientific papers

The Ireland-Claisen rearrangement as a probe for the diastereoselectivity of nucleophilic attack on a double bond adjacent to a stereogenic centre carrying a silyl group

The E- and Z-silyl enol ethers 4 derived from allyl 3-R-3-dimethyl(phenyl)silylpropanoate (R = Me, Pri and Ph) and the Z-silyl enol ethers 7 derived from 4-R-4-dimethyl(phenyl)silylbut-2-enyl acetate (R = Me and Pri) undergo Ireland-

The stereochemistry of the vinylogous Peterson elimination

Base-induced eliminations of the vinylogous β-hydroxysilanes 7, 9, 11 and 12 are stereospecifically syn, giving largely the trans,trans-diene 8 from 7 and 11, the cis,trans-diene 10 from 9, and the trans,cis-diene 13 from 12. When a cis double bond is produced, it is selectively placed adjacent to the carbon atom that originally carried the hydroxy group. E2′ Reactions with silyl as the electrofugal group and acetate as the nucleofugal group, initiated by fluoride ion, are not stereospecific, but can be highly stereoselective in favour of the trans,trans-diene 8 when the carbon substituent at the silicon-bearing end is a cyclohexyl group and the double bond is cis, and in favour of the trans,cis-diene 13 when the carbon substituent at the silicon-bearing end is a methyl group and the double bond is trans. Attempts to use the Peterson reactions to make o-quinodimethanes stereospecifically failed, with no evidence of 1,4-elimination from the alcohols 40 and 41. The corresponding E2′ reaction from the esters using fluoride ion on the acetates or formates 46 and 47 gave stereoselectively the E,E-quinodimethane 48.

A synthesis of enantiomerically enriched propargyl silanes

Reduction of ethyl 3-methyl-, 3-isopropyl- and 3-n-pentyl-3-[dimethyl(phenyl)silyl]propanoates 4 with DIBAL to the aldehydes 5, enol trifluoromethanesulfonate (triflate) formation using trifluoromethanesulfonic (triflic) anhydride and 2,6-di-tert-butylpyridine, and elimination using LDA, gives the propargyl silanes 8. The esters 4 could also be prepared enantiomerically enriched (11), and the final products are the enantiomerically enriched propargyl (homochiral) silanes 14.