205752-76-7

Upstream product

• 679410-18-5 1-trimethylsilyl-3-dimethyl(phenyl)silyl-4-methylpent-1-yne 
• 590-86-3 isovaleraldehyde 
• 166387-65-1 4-Methyl-1-(trimethylsilyl)-1-pentyne 
• 90701-59-0 1,1-Dibromo-4-methyl-1-pentene 

Downstream Products

• 679410-24-3 4-dimethyl(phenyl)silyl-5-methylhex-2-yn-1-ol 
• 679410-19-6 methyl 4-dimethyl(phenyl)silyl-5-methylhex-2-ynoate 
• 679410-21-0 (E)-5-methyl-4-dimethyl(phenyl)silylhex-2-en-1-ol 
• 679410-23-2 (E)-4-dimethyl(phenyl)silyl-5-methylhex-2-enyl acetate 
• 679410-25-4 4-dimethyl(phenyl)silyl-5-methylhex-2-ynyl acetate 
• 679410-12-9 {[(E)-1-Isopropyl-4-(1-trimethylsilanyloxy-vinyloxy)-but-2-enyl]-dimethyl-silanyl}-benzene 

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-

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.