324538-17-2

Upstream product

• 7787-20-4 (1R)-fenchone 
• 75-05-8 acetonitrile 
• 99749-00-5 lithioacetonitrile 
• 1195-79-5 (1R)-(-)-fenchone 

Downstream Products

• 439689-21-1 (E)-2-(1,3,3-trimethylbicyclo[2.2.1]hept-2-ylidene)acetonitrile 
• 439689-21-1 (Z)-2-(1,3,3-trimethylbicyclo[2.2.1]hept-2-ylidene)acetonitrile 
• 1602487-65-9 2-(2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)ethylcarbamoyl)phenylacetate 
• 1602487-68-2 (E)-3-(4-chlorophenyl)-N-(2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)ethyl)acrylamide 
• 1602487-69-3 N-(2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)ethyl)-3-phenylpropanamide 
• 1602487-71-7 N-(2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)ethyl)-P,P-diphenylphosphinicamide 
• 1602487-73-9 (E)-3-(4-(N-(2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)ethyl)sulfamoyl)phenyl)acrylic acid 
• 1602487-75-1 2-hydroxy-N-(2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)ethyl)benzamide 
• 1602487-78-4 2-amino-N-(2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)ethyl)benzamide 
• 1602487-79-5 2-(N,N-dimethylsulfamoylamino)-N-(2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)ethyl)benzamide 
• 1602487-81-9 dibenzyl [({2-[(1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]hept-2-yl]ethyl}amino)methylylidene]biscarbamate 
• 366014-01-9 (1R,2R,4S)-2-(2-aminoethyl)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol 
• 366014-01-9 (1R,2R)-2-(2-aminoethyl)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptane 

Relevant academic research and scientific papers

Functionalized organolithium reagents in the synthesis of chiral ligands for catalytic enantioselective addition of diethylzinc to aldehydes

Series of functionalized organolithium compounds were prepared and added to chiral bicyclic ketones (1R-(+)-camphor analogue 2 and 1R-(-)-fenchone 3), resulting in the preparation of a small library of chiral aminoalcohols able to serve as ligands in metal mediated asymmetric synthesis. The configuration of the chiral ligands was approved by applying advanced NMR experiments. The absolute configurations of 1,2-disubstituted planar chiral ferrocene-based aminoalcohols 15, 18 and 19 were determined by means of NMR experiments and confirmed by X-ray crystallography. The new chiral ligands were tested as pre-catalysts for the addition of diethyl zinc to benzaldehyde. The reactions proceeded with excellent conversions and a moderate degree of enantioselectivity.

Enantiopure antituberculosis candidates synthesized from (-)-fenchone

The synthesis of new enantiopure N-acyl compounds derived from (-)-fenchone has been performed. The evaluation of their in vitro activity against Mycobacterium tuberculosis H37Rv showed for most of them moderate activity. The structures bearing

Unsaturated nitriles: Stereoselective MgO eliminations

α,β-Unsaturated nitriles are readily synthesized by eliminating MgO from β-hydroxynitriles. Deprotonating acyclic, and cyclic, β-hydroxynitriles with excess MeMgCl smoothly generates dianion intermediates that eject MgO with concurrent formation of α,β-unsaturated nitriles. Alternatively, sequential addition of lithioacetonitrile and MgBr2 to aldehydes and ketones generates magnesium alkoxides in situ that eliminate MgO upon addition of MeMgCl. The MeMgCl-induced MgO eliminations smoothly generate α,β-unsaturated nitriles from hindered ketones that are otherwise difficult to synthesize.

Chiral β- and γ-aminoalcohols derived from (+)-camphor and (-)-fenchone as catalysts for the enantioselective addition of diethylzinc to benzaldehyde

The addition of Me3SiCN and LiCH2CN to (+)-camphor and (-)-fenchone, respectively, followed by reduction leads to chiral β- and γ-aminoalcohols. The enantioselectivities realized using these aminoalcohols as ligands in the addition of Et2Zn to benzaldehyde were lower than those obtained using the corresponding δ-aminoalcohols.