3197-43-1

Upstream product

• 934472-03-4 N-(5-hydroxy-1-methyl-pentyl)-4-methyl-benzenesulfonamide 
• 150197-74-3 (3S,6S)-6-((2S,4S,5R)-3,4-Dimethyl-5-phenyl-oxazolidin-2-yl)-3-methyl-3,6-dihydro-[1,2]oxazine-2-carboxylic acid benzyl ester 
• 142-83-6 trans,trans-2,4-Hexadienal 
• 150197-75-4 (2S,5S)-5-hydroxy-2-methylpiperidine 
• 155322-82-0 (3R,5S,8aS)-1-Benzyl-5-methyl-3-phenyl-octahydro-imidazo[1,2-a]pyridine 
• 119461-40-4 S-(+)-2-methyl-N-p-tosylaziridine 
• 934472-00-1 (S)-N-(hex-5-en-2-yl)-4-methylbenzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 3197-42-0 (S)-2-methylpiperidine 

Relevant academic research and scientific papers

An efficient approach to 2-substituted N-tosylpiperdines: asymmetric synthesis of 2-(2-hydroxy substituted)piperidine alkaloids

We have developed an efficient and a general approach to chiral 2-substituted N-tosylpiperidines starting from chiral α-substituted-N-tosylaziridines. Using this approach, we have synthesized (+)-coniine. The synthesis of chiral N-tosyl-2-piperidinylethanol 15 and ent-15, was achieved from l- and d-aspartic acids, respectively in few steps. Piperidine 15 was converted into 2-(2-hydroxysubstituted)piperidines of type 2 in optically active form. By applying this strategy, asymmetric syntheses of halosaline (R,R)-2a, (+)- and (-)-sedamine 2b, (+)- and (-)-allosedamine 2c, (+)- and (-)-sedridine 2d, (+)- and (-)-allosedridine 2e, (+)-tetraponerine T-3 3a, T-4 3c, T-7 3b, and T-8 3d have been achieved in high yields. These stereoisomers can be interconverted via Mitsunobu inversion in excellent yields.

2-(Penta-1,3-dienyl)oxazolidines: Synthesis of hydroxylated piperidines by a stereoselective Diels-Alder reaction

Hexa-2,4-dienal condensed with (-)-ephedrine to give predominantly the oxazolidine 4, which underwent a stereoselective Diels-Alder reaction with benzyl nitrosoformate to give the cycloadducts 9 and 10 in a ca 5:2 ratio. Further transformations of 9 to give the optically active mono- and tri-hydroxypiperidine derivatives 11 and 15 have also been performed.

A new route to homochiral piperidines

The synthesis of an enantiomeric pair of enaminoesters from phenylglycine is described. Conjugate addition to α,β-enones, reductive cyclization-fragmentation to octahydroimidazopyridines and further reduction to remove the auxiliary atoms, completes a new route to homochiral piperidines in which the enaminoesters function as homochiral 'ethanal enamines'.