New strategy for the asymmetric synthesis of phenyl ketone cyanohydrins: quaternization of cyanohydrins derived from 2-p-tolylsulfinyl benzaldehyde.
[reaction: see text] Optically pure functionalized cyanohydrins derived from 1-[2-(p-tolylsulfinyl)phenyl] ethanone can be obtained by the reaction of 2-p-tolylsulfinyl benzaldehyde derived cyanohydrins with bases and further treatment with suitable electrophiles. High yields and excellent stereoselectivities (up to de >98%) were obtained for these remote 1,4-asymmetric induction processes controlled by a sulfinyl chiral inductor.
García Ruano
José Luis
JL
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain. joseluis.garcia.ruano@uam.es
Martín-Castro
Ana M
AM
Tato
Francisco
F
Pastor
César J
CJ
D001547:Benzaldehydes / Q000737:chemistry; D009570:Nitriles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001547:Benzaldehydes; D009570:Nitriles; C430593:cyanohydrin