89656-79-1

Basic information

• Product Name: 1-Cyclohexene-1-carboxylic acid, 2-[[1-[(1,1-dimethylethoxy)carbonyl]-2-methylpropyl]amino]-, methyl ester, (S)-
• CAS NO: 89656-79-1
• Molecular Formula: C17H29NO4
• Molecular Weight: 311.422
• Mol File: 89656-79-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-Cyclohexene-1-carboxylic acid, 2-[[1-[(1,1-dimethylethoxy)carbonyl]-2-methylpropyl]amino]-, methyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclohexene-1-carboxylic acid, 2-[[1-[(1,1-dimethylethoxy)carbonyl]-2-methylpropyl]amino]-, methyl ester, (S)-(89656-79-1)
• EPA Substance Registry System: 1-Cyclohexene-1-carboxylic acid, 2-[[1-[(1,1-dimethylethoxy)carbonyl]-2-methylpropyl]amino]-, methyl ester, (S)-(89656-79-1)

Safety Data

• Hazardous Substances Data: 89656-79-1(Hazardous Substances Data)

Upstream product

• 13211-31-9 tert-butyl L-valinate 
• 41302-34-5 2-(methoxycarbonyl)cyclohexanone 

Downstream Products

• 89708-65-6 methyl (R)-1-allyl-2-oxocyclohexanecarboxylate 
• 58648-11-6 methyl (S)-1-allyl-2-oxocyclohexanecarboxylate 
• 58648-10-5 ethyl (S)-1-allyl-2-oxocyclohexane-1-carboxylate 
• 148260-33-7 ((1R)-2c-carboxy-2t-methyl-cyclohex-r-yl)-acetic acid 
• 89656-83-7 (S)-(+)-methyl 1-methyl-2-oxocyclohexanecarboxylate 
• 89656-84-8 methyl (S)-1-benzyl-2-oxocyclohexanecarboxylate 
• 89656-88-2 methyl (R)-1-benzyl-2-oxocyclohexanecarboxylate 
• 89656-82-6 methyl (-)-(R)-2-methyl-1-oxocyclohexane-2-carboxylate 

Relevant articles and documents

Stereoselective reactions. XXI. Asymmetric alkylation of α-alkyl β-keto esters to α,α-dialkyl β-keto esters having either (R)- Or (S)-chiral quaternary center depending on the solvent system

Asymmetric alkylation reaction of chiral enamines prepared from α-alkyl β-keto esters and (S)-valine tert-butyl ester leading to either enantiomer is described. Lithiated chiral enamines can be alkylated with alkyl halides in a toluene solvent in the presence of HMPA to give, after hydrolysis, α,α-dialkyl β-keto esters in 70-99%ee. The reactions in the presence of THF, dioxolane, or trimethylamine, instead of HMPA, afford the corresponding antipodes with enantiomeric purities of 44-92%ee. The present method provides a procedure for the synthesis of both enantiomers of α,α-dialkyl β-keto esters in high enantiomeric purities starting from the same chiral enamines.

Construction of Contiguous Quaternary and Tertiary Carbon Centres via the Asymmetric Michael Reaction

Michael reactions of chiral lithioenamines of α-alkyl β-oxo esters with methyl ethylidenemalonate afforded, after hydrolysis, adducts having contiguous quaternary and tertiary carbon centres, with nearly complete enantio- and diastereo-selectivity.