217460-28-1

Upstream product

• 105-30-6 (S)-2-methyl-1-pentanol 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 105-30-6 (R)-2-methylpentan-1-ol 
• 217460-27-0 (2S,2'S)-2-methoxymethyl-1-(2'-methyl-1'-pentylideneamino)pyrrolidine 
• 53531-14-9 (R)-(+)-2-methylpentanal 
• 82043-22-9 (S)-(-)-2-methylpentanal 
• 59983-39-0 (S)-1-amino-2-(methoxymethyl)pyrrolidine 
• 72748-99-3 (R)-1-Amino-2-(methoxymethyl)pyrrolidine 
• 737776-63-5 (R)-2-Methoxymethyl-1-(1'-propylidenamino)-pyrrolidine 
• 72203-94-2 N-[(S)-2-methoxymethylpyrrolidin-1-yl]propan-1-imine 

Relevant academic research and scientific papers

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%).

The total synthesis of (+)-pectinatone: An iterative alkylation approach based on the SAMP-hydrazone method

The marine natural product (+)-pectinatone containing 'skip' 1,3- dimethyl stereocentres was synthesised via the iterative alkylation of propanal SAMP-hydrazone with β-branched iodides. Factors affecting the selectivity of the alkylation reaction and the in situ formation of volatile β-branched iodides are described.