308356-93-6

Upstream product

• 308356-90-3 (R)-4-Propyl-[1,3,2]dioxathiane 2,2-dioxide 
• 170956-17-9 (S)-1-[(4-methylphenyl)sulfonyl]-2-propylaziridin 
• 934472-24-9 4-methyl-N-(1-propyl-pent-4-enyl)-benzenesulfonamide 
• 308356-92-5 (S)-6-Propyl-1-(toluene-4-sulfonyl)-piperidin-2-one 
• 308356-91-4 (S)-6-Propyl-1,3-bis-(toluene-4-sulfonyl)-piperidin-2-one 
• 84314-30-7 (R)-(-)-hexane-1,3-diol 

Downstream Products

• 60343-68-2 N-Tosyl coniine 
• 458-88-8 coniine 

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.

Asymmetric piperidine synthesis via 1,3-cyclic sulfates

Cyclic sulfates undergo a double alkylation with stabilized C,N-dianions derived from 3a/b to provide the piperidine ring system. The 4-substituted variant 7 affords a formal but stereochemically efficient synthesis of (S)-coniine.