163877-34-7

Upstream product

• 583-60-8 2-Methylcyclohexanone 
• 107-13-1 acrylonitrile 
• 352695-16-0 (1R_.E)-N-(2-methylcyclohexylidene)-1-phenylethanamine 

Downstream Products

• 53068-89-6 (R)-(+)-2-(2'-carbomethoxyethyl)-2-methylcyclohexanone 
• 207725-74-4 3-((R)-4-Methyl-2-trimethylsilanyl-1-oxa-spiro[2.5]oct-4-yl)-propionitrile 
• 91306-30-8 (R)-(+)-2-methyl-2-(3-oxobutyl)cyclohexanone 
• 1380600-15-6 (R)-benzyl 3-(1-methyl-2-oxocyclohexyl)propanoate 
• 207725-78-8 3-[(R)-2-Hydroxy-2-(hydroxy-trimethylsilanyl-methyl)-1-methyl-cyclohexyl]-propionitrile 
• 218899-31-1 4-{(R)-1-Methyl-2-[1-trimethylsilanyl-meth-(Z)-ylidene]-cyclohexyl}-butan-2-one 
• 207725-80-2 3-[(R)-2-(Bromo-trimethylsilanyl-methyl)-2-hydroxy-1-methyl-cyclohexyl]-propionitrile 
• 218899-29-7 3-{(R)-1-Methyl-2-[1-trimethylsilanyl-meth-(Z)-ylidene]-cyclohexyl}-propionitrile 

Relevant academic research and scientific papers

Construction of Stereogenic α,α-Disubstituted Cycloalkanones via 1° Amine Thiourea Dual Catalysis: Experimental Scope and Computational Analyses

The mechanistic exploration and an expanded experimental discussion of the organocatalyzed, asymmetric Pfau-dAngelo reaction by exploiting a bifunctional 1° amine thiourea catalyst system is disclosed. Notable breadth in substrate scope has been demonstrated on both the cyclic ketone moiety and the α,β-unsaturated electrophile. Exploration into the matched and mismatched selectivity of this process with a ketone containing pre-existing stereocenters has been demonstrated. Computational analyses of the reaction mechanism are reported. In concert with kinetic isotope effect (KIE) experiments, these computational results provide a detailed understanding of the likely mechanism, including the aspects of the organocatalyst scaffold that are critical for stereoselectivity.

Enantioselective Synthesis of Quaternary Carbon Stereogenic Centers through the Primary Amine-Catalyzed Michael Addition Reaction of α-Substituted Cyclic Ketones at High Pressure

The enantioselective Michael addition reaction of α-substituted cyclic ketones with acrylates was efficiently promoted by a primary amine chiral catalyst under high-pressure conditions (1.0 GPa) in tetrahydrofuran. This method was highly successful for the construction of an all-carbon-substituted quaternary-carbon stereogenic center at the α-position of cyclic ketones in high enantiomeric excess, and could be conveniently applied to the formal synthesis of (+)-aspidospermidine. The Michael addition reaction of α-substituted cyclic ketones was efficiently promoted by a primary amine-based organocatalyst under high-pressure conditions (1.0 GPa) in tetrahydrofuran.

Primary amine, thiourea-based dual catalysis motif for synthesis of stereogenic, all-carbon quaternary center-containing cycloalkanones

The enantioselective synthesis of α,α-disubstituted cycloalkanones has been developed using a primary amine, thiourea-based dual catalysis pathway. A range of electrophiles and ring sizes are tolerated under the reaction conditions. A possible catalytic c

The asymmetric Michael reaction involving chiral imines: Use of acrylonitrile as acceptor and subsequent functionalization of the adducts

Condensation of chiral imines 1 and acrylonitrile led to adduct (R)-6 with an ee ≥ 95%. This adduct has then been converted into chiral synthons 9, 11, 12 and 17.