66581-82-6

Upstream product

• 917-64-6 methyl magnesium iodide 
• 61157-35-5 2-chloro-3-phenylpropionyltrimethylsilane 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 70280-48-7 3-benzyl-5-chloro-4-methoxy-2-pentanone 
• 62731-45-7 1-hydroxy-1,5-diphenyl-pentan-3-one 
• 62730-80-7 2-benzyl-1-hydroxy-1-phenyl-3-butanone 
• 70280-44-3 3-benzyl-4-hydroxy-2-dodecanone 
• 70280-38-5 5-hydroxy-1-phenyl-3-tridecanone 

Relevant academic research and scientific papers

The highly enantioselective transformation of silylketenes into α-silylthioesters catalysed by cinchona alkaloids

The reaction of silylketenes with thiophenol, mediated by cinchona alkaloid catalysts, proceeds to give α-silylthioester products in good chemical yield and with enantiomeric excess values in the range 79-93%. The absolute configuration of one of the thioester products was determined by X-ray diffraction.

Reactions of 2-Chloroacyltrimethylsilanes with Grignard Reagents. Preparation of 3-(Trimethylsilyl)-2-alkanones and 2-(Trimethylsilyl)-1-alkanols

Reactions of 2-chloroacyltrimethylsilanes with Grignard reagents have been examined.Thus, treatment with methylmagnesium iodide affords the corresponding 3-(trimethylsilyl)-2-alkanones through an initial addition followed by removal of chloride anion and 1,2-rearrangement of silyl group.In contrast, the reaction proceeds with 2 equiv of the Grignard reagents bearing β-hydrogen to give 2-(trimethylsilyl)-1-alkanols, where initial reduction of the silylcarbonyl group followed by such rearrangement and addition of the Grignard reagents to the resulting 2-(trimethylsilyl)alkanals have been proposed.

Aldol Reactions with α-Trimethylsilyl Ketones. Dual Roles of the Trimethylsilyl Group for Regiospecific Generation of Enolate Equivalents

Aldol reactions of α-trimethylsilyl ketones, R1CH(SiMe3)COCH2R2, with aldehydes or acetals have been examined under Lewis acidic and basic conditions.In the presence of stannic chloride or boron trifluoride etherate, α-trimethylsilyl ketones react with aldehydes or acetals on the carbon bearing the silyl group exclusively to afford the corresponding addition products.On the other hand, lithium diisopropylamide usually deprotonates the opposite carbon atom to generate enolates, R1CH(SiMe3)C(OLi)=CHR2, selectively, which yield another type of aldol product after removal of the silyl group.Thus, two types of aldols can be prepared regioselectively from common α-trimethylsilyl ketones.