276239-73-7

Upstream product

• 676-58-4 methylmagnesium chloride 

Downstream Products

• 276240-09-6 (1R,2R,6S)-(+)-2-(6-methyl-2-vinyl-3,6-dihydro-2H-pyridin-1-yl)-2-phenylethanol 
• 276240-13-2 (2R,2R,6S)-2-(6-methyl-2-trimethylsilanylmethyl-3,6-dihydro-2H-pyridin-1-yl)-2-phenylethanol 
• 276240-12-1 (2S,2R,6S)-(+)-2-[2-(2-[1,3]-dioxolan-2-yl-ethyl)-6-methyl-3,6-dihydro-2H-pyridin-1-yl]-2-phenylethanol 
• 276240-11-0 (1R,2S,6S)-(+)-(6-methyl-2-undecyl-3,6-dihydro-2H-pyridin-1-yl)-2-phenylethanol 
• 276239-82-8 (1R,2S,3S,4R,6S)-(-)-6-[2-[1,3]-dioxolan-2-ylethyl]-1-(2-hydroxy-1-phenylethyl)-2,4-dimethylpiperidin-3-ol 
• 276239-81-7 (2S,2R,4S,5R,6S)-(+)-2-{2-[2-[1,3]-dioxolan-2-yl-ethyl]-6-methyl-4,5-epoxy-3,6-dihydro-2H-pyridin-1-yl}-2-phenylethanol 
• 129784-74-3 (5S,9R)-5-methylindolizidine 

Relevant academic research and scientific papers

Stereocontrolled alkylation of chiral pyridinium salt toward a short enantioselective access to 2-alkyl- and 2,6-dialkyl-1,2,5,6- tetrahydropyridines

Treatment of salts 1a-b with Grignard reagents gives, after reduction of the resulting unstable dihydropyridines 7, the tetrahydropyridines 8a-c, with modest selectivities but in very few steps and under practical conditions. Higher stereo and regioselectivities are obtained with salt 1c which gives the tetrahydropyridines 15a-e. In addition, the dihydropyridine intermediates 11b cyclize to give the new oxazolidine derivatives 12a-e, which turn out to be good precursors of the 2,6-trans-disubstituted tetrahydropyridines 21a-e. Selective syntheses of (-)-lupetidin, (+)-solenopsin, and indolizidines (-)-5 and (-)-6 are presented as representative examples of applications.