| Reference: | Boyer, F. D.; Hanna, I.; Ricard, L. Org. Lett. 2004, 6, 1817. DOI |
| Keywords: | Pd/Sn-Vinyl+Vinyl-X • Stille coupling • Michael EneNitrile • Ketone enolate+EneNitrile • Reductive cyanation • Li-Isocyanide • Li/H -> Li-Alkynyl • O-H -> O-SiMe2tBu • EnoateEster -> Allyl-OH • O-SiMe2tBu -> O-H • Diol -> Ketal • Allyl-OH -> Enone • Seyferth-Gilbert homologation • Aldehyde -> Alkyne • Li-Nitrile+Alkyl-X • Li-Alkynyl+Chlorocarbonate • Enyne metathesis • Nitrile+Mg-Alkyl -> Ketone • Mg-Alkyl+Nitrile • Nitrile -> Aldehyde • Epoxide -> Allyl-OH • Ketone -> Vinyl-OTf • Epoxidation, peracid • Mechanism • |
| Reagents: | Acrylonitrile • NaOMe • Pyridine, 2,6-di-tBu • Pd(PPh3)4 • TsCH2NC • LiN(SiMe3)2 • AlHiBu2 • Diazophosphonate • Carbonate, potassium • BuLi(n) • Perbenzoic acid, 3-chloro • Yb(OTf)3 • SiMe2tBu-OTf • AlHiBu2 • Fluoride, Bu4N+ • Me2C(OMe)2 • Dess-Martin • Grubbs II • NiCl2 • O=C(OR)Cl • KOtBu • DMSO (solvent) • |