Modified Fry Cyanation of a Chiral Pyridinium Salt: Asymmetric Syntheses of (-)-Coniine and (-)-Solenopsin A - Université de Rennes Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2013

Modified Fry Cyanation of a Chiral Pyridinium Salt: Asymmetric Syntheses of (-)-Coniine and (-)-Solenopsin A

Résumé

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.

Domaines

Chimie organique

Dates et versions

hal-00866525 , version 1 (26-09-2013)

Identifiants

Citer

Van Ha Vu, Laurie-Anne Jouanno, Adèle Cheignon, Thierry Roisnel, Vincent Dorcet, et al.. Modified Fry Cyanation of a Chiral Pyridinium Salt: Asymmetric Syntheses of (-)-Coniine and (-)-Solenopsin A. European Journal of Organic Chemistry, 2013, 2013 (24), pp.5464-5474. ⟨10.1002/ejoc.201300595⟩. ⟨hal-00866525⟩
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