138235-01-5

Upstream product

• 94286-28-9 4-(dimethylphenylsilyl)-3-phenylpropanoic acid methyl ester 
• 148003-99-0 benzyl (3RS)-3-dimethyl(phenyl)silyl-3-phenylpropanoate 
• 4192-77-2 ethyl cinnamate 
• 3839-31-4 dimethyl(phenyl)silyllithium 
• 103-26-4 Methyl cinnamate 

Downstream Products

• 100-42-5 styrene 
• 144452-46-0 3-(Dimethyl-phenyl-silanyl)-3-phenyl-propionyl chloride 
• 679410-36-7 (E)-but-2-enyl 3-phenyl-3-dimethyl(phenyl)silylpropanoate 
• 212180-93-3 4-(Dimethyl-phenyl-silanyl)-4-phenyl-butyryl azide 

Relevant academic research and scientific papers

A study on the influence of a silicon group on the Curtius reaction

The effect of a dimethyl(phenyl)silyl group at different positions with respect to an acyl azide moiety on the Curtius reaction has been investigated. A silyl group at the β-position enhanced the reaction rate by about three times compared to a non-silylated analog. However, a silyl group at the γ-position had only a minor influence on the reaction. A diacyl azide having a silyl group at the β-position with respect to one acyl azide group and at the γ-position with respect to the other acyl azide group has been prepared and subjected to the Curtius reaction in order to evaluate the possible synthetic potential which originates from the control exerted by the silicon group in such systems.

Diastereoselectivity in the Preparation of β-Silyl Esters from αβ-Unsaturated Esters and Amides Attachhed to Chiral Auxiliaries

The conjugate addition of the phenyldimethylsilyl-cuprate reagent to cinnamate and crotonate esters and amides 1 of various known chiral auxiliaries, a-e, is diastereoselective.The sense of diastereoselectivity of silyl-cuprate addition to the esters 1b-d, 8 and 9 is different from established precedent based on carbon-cuprates, but is normal for silyl-cuprate addition to the amide 1a, the imines 1e and 21, and the oxazolidine 6.The chiral auxiliary e gives the best results of those tested, and the silicon-containing group can be removed from the chiral auxiliary using alkoxide ion in aprotic media, making available β-silyl esters 27-29 of high enantiomeric excess, with recovery of the chiral auxiliary 30.

Formation of 3-azetidin-2-ones: Stereocontrolled Formal Approach to (+/-)-Thienamycin and (+/-)-β-(Hydroxyalkyl)aspartic Acid Derivatives

Reaction between (+/-)-β-(dimethylphenylsilyl)alkanoyl chlorides and imines of glyoxylic esters provided a route to (+/-)-cis-3--4-alkoxycarbonyl β-lactams, while addition of the Fleming's silylcuprate reagent to methyl crot