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Modified Fry Cyanation of a Chiral Pyridinium Salt: Asymmetric Syntheses of (–)‐Coniine and (–)‐Solenopsin A
Author(s) -
Vu Van Ha,
Jouanno LaurieAnne,
Cheig Adèle,
Roisnel Thierry,
Dorcet Vincent,
Sinbandhit Sourisak,
Hurvois JeanPierre
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300595
Subject(s) - chemistry , cyanation , pyridinium , yield (engineering) , alkylation , piperidine , salt (chemistry) , lithium (medication) , enantiomer , hydride , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , hydrogen , materials science , metallurgy , endocrinology , medicine
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 of piperidine alkaloids (–)‐coniine and (–)‐solenopsin A.