84247-82-5

Upstream product

• 100-52-7 benzaldehyde 
• 61518-50-1 1,3-bis(trimethylsilyl)prop-1-enyl-lithium 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 2612-42-2 (dibromomethyl)trimethylsilane 
• 106-95-6 allyl bromide 
• 17891-78-0 2,2,6,6-tetramethyl-2,6-disila-3-heptene 
• 14371-10-9 (E)-3-phenylpropenal 
• 3739-98-8 triphenyl(trimethylsilylmethyl)phosphonium iodide 
• 18178-59-1 (E)-1,2-bis(trimethylsilyl)ethene 
• 42599-24-6 E-styryl iodide 

Relevant academic research and scientific papers

The Synthesis of Alkenes from Carbonyl Compounds and Carbanions α to Silicon. Stereoselective Synthesis of 1-Trimethylsilylbuta-1,3-dienes

Reactions of aldehydes with the 1,3-bis(trimethylsilyl)propenyl anion in the presence of magnesium bromide or trimethyl borate give stereoselectively the alcohols (2) which can be transformed stereospecifically to either (1E,3E)- or (1E,3Z)-1-trimethylsilylbuta-1,3-dienes.

Preparation of silyl-substituted dizinciomethanes and their reactions with electrophiles

Silyl-substituted bis(bromozincio)methanes (RMe2Si-CH(ZnBr)2; R = Me, Ph, and p-MeO-C6H4), prepared from the corresponding dibromides by Pb catalyzed reaction with zinc, reacted stepwise with two different electrophiles, R1X and E+, yielding R1- CH(SiMe2R)-E.

Alkylidenation of carbonyl compounds with gem-dizincioalkanes mediated with titanium dichloride

Olefination of carbonyl compounds with gem-dizincio-alkanes, bis(iodozincio)methane, 1,1-bis(iodozincio)ethane, and bis(bromozincio)methyltrimethylsilane, afforded the corresponding olefins in good to excellent yields.

Formation of 1-(Trimethylsilyl) 1,4-Dienes by Vinylation of Allyltrimethylsilane in the Presence of the Palladium(0)/Silver Salt System

The major products formed in palladium-catalyzed reactions of allyltrimethylsilane with vinyl iodides, in the presence of silver ion or with vinyl triflates are 1-(tri-methylsilyl) 1,4-dienes.In the absence of silver salts, only traces of these dienes are formed, and desilylation is predominant.Addition of silver salts enhances the reaction rate, suppresses the desilylation, and affects the isomer distribution.The isolated yields of the 1-(trimethylsilyl) 1,4-dienes are, in general, low owing to unfavourable regioselectivity in the reactions.

SYNTHESIS OF χ,δ-UNSATURATED α-AMINO ACIDS FROM ALLYLSILANES AND GLYCIDYL CATION EQUIVALENTS

The synthesis of a series of χ,δ-unsaturated N-protected α-amino acid methylesters from the coupling of different allylsilanes and glycidyl cation equivalents 6 and 7 is described.Reactions with methoxyglycine derivative 6 are induced with BF3*OEt2; in the case of chloroglycine derivative 7 SnCl4 is used as Lewis acid.Reactions are fully regioselective, but show low stereoselectivity.The conversion of the reaction products into unprotected α-amino acids is described for two cases.