First highly stereoselective synthesis of fungicide systhane.
[reaction: see text] Highly enantiopure (R)-2-p-chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile 1 (myclobutanil or systhane) was obtained in six synthetic steps from commercially available 1-hexyne (35% yield, 92% ee). The sulfinyl group controls the two key steps of the synthetic sequence, the highly stereoselective hydrocyanation of vinyl sulfoxides with Et(2)AlCN and the further introduction of the proper functionality into the molecule.
García Ruano
José L
JL
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain. joseluis.garcia.ruano@uam.es
Cifuentes García
Marta
M
Martín Castro
Ana M
AM
Rodríguez Ramos
Jesús H
JH
D005659:Fungicides, Industrial / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009570:Nitriles / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis*
D005659:Fungicides, Industrial; D007202:Indicators and Reagents; D009570:Nitriles; D014230:Triazoles; C446685:systhane