191422-43-2

Basic information

• Product Name: methyl (R_S,3S,4R)-3-methyl-4-(p-tolylsulfinyl)-5-trimethylsilylpentanoate
• Synonyms: methyl (R_S,3S,4R)-3-methyl-4-(p-tolylsulfinyl)-5-trimethylsilylpentanoate
• CAS NO: 191422-43-2
• Molecular Weight: 340.559
• Mol File: 191422-43-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl (R_S,3S,4R)-3-methyl-4-(p-tolylsulfinyl)-5-trimethylsilylpentanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (R_S,3S,4R)-3-methyl-4-(p-tolylsulfinyl)-5-trimethylsilylpentanoate(191422-43-2)
• EPA Substance Registry System: methyl (R_S,3S,4R)-3-methyl-4-(p-tolylsulfinyl)-5-trimethylsilylpentanoate(191422-43-2)

Safety Data

• Hazardous Substances Data: 191422-43-2(Hazardous Substances Data)

Upstream product

• 623-43-8 crotonic acid methyl ester 
• 153123-09-2 (R_S)-p-Tolyl β-(trimethylsilyl)ethyl sulfoxide 

Relevant articles and documents

Extremely Efficient Chiral Induction in Conjugate Additions of p-Tolyl α-Lithio-β-(trimethylsilyl)ethyl Sulfoxide and Subsequent Electrophilic Trapping Reactions

Reaction of p-tolyl α-lithio-β-(trimethylsilyl)ethyl sulfoxide with α,β-unsaturated esters gave the conjugate addition products as a single diastereomer. The intermediate enolates were subsequently trapped with various alkyl halides or aldehydes to give the products with extremely high stereoselectivity. The reaction with α,β-unsaturated ketones also proceeded with high diastereoselectivity. Protolysis of the enolates derived from the α-methyl-α,β-unsaturated esters gave the products with high stereoselectivity. The stereo- and regioselective elimination of the sulfinyl group gave chiral homoallylic carboxylates.