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

…, LA Jouanno, A Cheignon, T Roisnel…

Index: Vu, Van Ha; Jouanno, Laurie-Anne; Cheignon, Adele; Roisnel, Thierry; Dorcet, Vincent; Sinbandhit, Sourisak; Hurvois, Jean-Pierre European Journal of Organic Chemistry, 2013 , # 24 p. 5464 - 5474

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Citation Number: 2

Abstract

Abstract The synthesis of chiral 2-cyano-Δ 4-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 ...