348608-13-9Relevant academic research and scientific papers
Modified fry cyanation of a chiral pyridinium salt: Asymmetric syntheses of (-)-coniine and (-)-solenopsin A
Vu, Van Ha,Jouanno, Laurie-Anne,Cheignon, Adele,Roisnel, Thierry,Dorcet, Vincent,Sinbandhit, Sourisak,Hurvois, Jean-Pierre
, p. 5464 - 5474 (2013/09/02)
The synthesis of chiral 2-cyano-Δ4-tetrahydropyridine 5 was carried out in 85 % yield through a modified two-step Fry reductive cyanation of pyridinium salt (+)-3c that used lithium triethylborohydride as the hydride donor. An alkylation-reduction sequence provided 2-alkyl-substituted tetrahydropyridines (+)-10a and (+)-10b in 72-75 % yield after chromatographic purification. This protocol has been applied to the asymmetric syntheses of piperidine alkaloids (-)-coniine and (-)-solenopsin A. The two-step reductive cyanation of chiral pyridinium salt (+)-3c afforded α-amino nitrile 5 in 85 % yield, which underwent an alkylation-reduction sequence followed by removal of the chiral moiety to yield the hemlock alkaloid (-)-coniine as its mandelate salt (>99:1 er). This reaction sequence was also used for the synthesis of the trans-2,6-disubstituted piperidine alkaloid (-)-solenopsin A. Copyright
Synthesis of (-)-coniine and (-)-pipecoline using ruthenium catalyzed ring closing metathesis
Pachamuthu, Kandasamy,Vankar, Yashwant D.
, p. 359 - 363 (2007/10/03)
Ring closing metathesis employing the well-known Grabbs' ruthenium catalyst has been used as the key step in the synthesis of piperidine alkaloids, (-)-coniine and (-)-pipecoline, and the asymmetric induction has been performed by using (R)-α-methyl benzy
