123930-76-7

Upstream product

• 66334-32-5 (R)-(-)-2-methyl-2-(4-methylphenyl)-4-oxopentanal 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 124018-43-5 5-methyl-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one 
• 1311260-04-4 tert-butyl (2-(p-tolyl)but-3-en-2-yl) carbonate 
• 1311260-43-1 (S)-1-(3,5-dimethylhexa-1,5-dien-3-yl)-4-methylbenzene 
• 51431-59-5 2-(p-tolyl)but-3-en-2-ol 
• 122-00-9 para-methylacetophenone 
• 624-31-7 4-tolyl iodide 
• 133678-92-9 (2R)-2-methyl-2-(4-methylphenyl)pentane-1,4-diol 
• 515844-94-7 (R_S)-(E)-1-chloro-2-(4-methylphenyl)-1-(p-tolylsulfinyl)-1-propene 
• 795277-33-7 1-[(E)-(S)-3-Isopropenyloxy-3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-1-methyl-propenyl]-4-methyl-benzene 
• 795277-39-3 (E)-(S)-6-((1S,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-4-methyl-4-p-tolyl-hex-5-en-2-one 
• 795278-37-4 Acetic acid (E)-(S)-1-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-3-p-tolyl-but-2-enyl ester 
• 795280-30-7 (E)-(S)-1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-3-p-tolyl-but-2-en-1-ol 

Downstream Products

• 123930-77-8 (S)-4,5,5-trimethyl-4-(4-methylphenyl)-2-cyclopentenone 
• 169305-53-7 (R)-4,5-dimethyl-4-p-tolylcyclopentenone 

Relevant academic research and scientific papers

Synthesis of Cyclopentenones with C4-Quaternary Stereocenters via Stereospecific [3,3]-Sigmatropic Rearrangement and Applications in Total Synthesis of Sesquiterpenoids

A cationic gold(I)-catalyzed asymmetric [3,3]-sigmatropic rearrangement of sulfonium leads after cyclization to cyclopentenones with a C4-quaternary stereocenter. Starting with simple vinyl sulfoxides and propargyl silane, numerous compounds were isolated

Enantioselective construction of all-carbon quaternary centers by branch-selective Pd-catalyzed allyl-allyl cross-coupling

The Pd-catalyzed cross-coupling of racemic tertiary allylic carbonates and allylboronates is described. This reaction generates all-carbon quaternary centers in a highly regioselective and enantioselective fashion. The outcome of these reactions is consistent with a process that proceeds by way of 3,3′-reductive elimination of bis(η1-allyl)palladium intermediates. Strategies for distinguishing the product alkenes and application to the synthesis of (+)-α-cuparenone are also described.

p-menthane-3-carboxaldehyde: A useful chiral auxiliary for the synthesis of chiral quaternary carbons of high enantiomeric purity

(+)- or (-)-p-Menthane-S-carboxaldehyde is made in two easy steps from (+)- or (-)-menthone, respectively. This auxiliary allows for the synthesis of carbonyl compounds bearing a α-chiral quaternary carbon. The flexibility, efficiency, and ease of use of

A novel method for the asymmetric synthesis of 4,4-disubstituted 2-cyclopentenones from optically active 1-chlorovinyl p-tolyl sulfoxides and its application to the asymmetric total synthesis of (+)-α-cuparenone

Enantiomerically pure 1-chlorovinyl p-tolyl sulfoxides having two different substituents at the 2-position were synthesized from unsymmetrical ketones and (R)-(-)-chloromethyl p-tolyl sulfoxide in three steps. Treatment of the 1-chlorovinyl p-tolyl sulfoxides with cyanomethyllithium at -78°C to room temperature gave optically active 2-amino-1-cyano-5,5-disubstituted-1,3-cyclopentadienes in high yields with very high asymmetric induction from the stereogenic center of the sulfoxide moiety. A mechanism for the asymmetric induction is proposed. The products were treated with phosphoric acid in acetic acid at reflux temperature to give enantiomerically pure 4,4-disubstituted 2-cyclopentenones in good yields. As an application of this synthetic method, a relatively short (seven steps) total asymmetric synthesis of (+)-α-cuparenone from methyl 4-methylphenyl ketone is described.

Asymmetric Construction of Quaternary Carbons from Chiral Malonates: Selective and Versatile Total Syntheses of the Enantiomers of α- and β-Cuparenones from a Common Optically Active Precursor

From a single chiron (R)-4, available with high enantiomeric purity (96percent) by simple enzymatic hydrolysis (PLE) of a prochiral malonate, were prepared convenient precursors of the two enantiomers of α- and β-cuparenones (1a,b and 2a,b).This versatile

Enantioconvergent Route to α-Cuparenone from Dicyclopentadiene

A formal enantioconvergent route to α-cuparenone from dicyclopentadiene has been devised by employing lipase catalysed kinetic hydrolysis as the key step.