737776-63-5

Upstream product

• 72748-99-3 (R)-1-Amino-2-(methoxymethyl)pyrrolidine 
• 123-38-6 propionaldehyde 

Downstream Products

• 7786-29-0 (R)-α-methyloctanal 
• 254435-67-1 (R)-2-methyl-octyl toluene-4-sulfonate 
• 217460-28-1 (S)-(+)-2-methylpentyl p-nitrophenylsulfonate 
• 105-30-6 (R)-2-methylpentan-1-ol 
• 105-30-6 (S)-2-methyl-1-pentanol 
• 326591-12-2 (R)-(-)-2-methylpentyl p-nitrophenylsulfonate 

Relevant academic research and scientific papers

First asymmetric synthesis of both enantiomers of Tropional and their olfactory evaluation

The first asymmetric synthesis of both enantiomers of Tropional is accomplished by asymmetric alkylation by employing the SAMP/RAMP-hydrazone method, respectively. The alkylated hydrazones were oxidatively cleaved with magnesium-monoperoxyphthalate (MMPP). Subsequent reduction of the resulting nitriles with diisobutyl aluminium hydride (DIBAL-H) led to the desired aldehydes in good overall yields (52-53%) and enantiomeric excesses (ee=90%). Furthermore, the olfactory evaluation of both enantiomers showed remarkable differences in odour quality and intensity.

Asymmetric synthesis of all stereoisomers of 7,11-dimethylheptadecane and 7-methylheptadecane, the female pheromone components of the spring hemlock looper and the pitch pine looper

The asymmetric synthesis of the stereoisomers of 7,11-dimethylheptadecane (1) and 7-methylheptadecane (2) via α-alkylation employing the SAMP/RAMP hydrazone method with high asymmetric induction and good overall yields is described. A mixture of (7S,11R)-1 and (S)-2 is the female-produced sex pheromone of the spring hemlock looper moth (Lambdina athasaria) and the pitch pine looper moth (Lambdina pellucidaria). They are both forest pests in northeastern North America.

First asymmetric synthesis of 6-methyl-3-nonanone, the female-produced sex pheromone of the caddisfly Hesperophylax occidentalis

The asymmetric synthesis of the female-produced sex pheromone of the caddisfly Hesperophylax occidentalis, (S)-and (R)-6-methyl-3-nonanone, starting from the simple starting materials propanal, propyl iodide and 2-butanone, in good overall yields is described. The stereogenic centre at the C-6 position of the pheromone was generated via α-alkylation employing the SAMP/RAMP hydrazone method with high asymmetric induction (ee = 94 and 92%).

ASYMMETRIC MICHAEL ADDITIONS VIA SAMP-/RAMP-HYDRAZONES ENANTIOSELECTIVE SYNTHESIS OF PHEROMONES OF THE SMALL FOREST ANT (FORMICA POLYCTENA) AND THE RED WOOD ANT (F. RUFA)

A simple and efficient asymmetric synthesis of the pheromones of the small forest ant (Formica polyctena) and the red wood ant (F. rufa) is described.The key step is an asymmetric Michael addition of lithiated propanal-SAMP- or RAMP-hydrazone to enoates with virtually complete asymmetric induction (de,ee 96percent).