Reference: | Zakarian, A.; Batch, A.; Holton, R. A.. J. Am. Chem. Soc. 2003, 125, 7822-7823. DOI (Part 2) |
Keywords: | Alkene cleavage Aldehyde → Alkyl-OH CarboxEster → CarboxAcid Henbest Diol-1,3 → Acetal EnoateEster → Allyl-OH Epoxide reduction Hydroboration alkene Diol-1,3 → Acetal O-H → O-MOM Acetal → Diol O-Bn → O-H O-H → O-Tf CarboxEster → CarboxAcid O-H → O-SiiPr3 CarboxEster → CarboxAcid Iodolactonization CarboxEster enolate+Alkyl-X Alkyl-X+Enolate Alkyl-OH → Alkyl-I Epoxidation, peracid Lemieux-Johnson oxidation Furst-Plattner diaxial Sn-Allyl+Allyl-X Allyl-X+Sn-R Pd/Zn-Alkyl+Vinyl-X Negishi coupling Alkyne Silyl-metalation Si-Vinyl → I-Vinyl Li-Alkynyl+Alkyl-X Li/H → Li-Alkynyl Alkyl-X+Li-R |
Reagents: | SnBu2(O) NaH Camphor sulfonic acid LiNiPr2 OsO4, NaIO4 BH3CN-Na+ PPh3, I2 Allyl-SnR3 BF3·OEt2 NaOMe Perbenzoic acid, 3-chloro Camphor sulfonic acid AlHiBu2 AlH4-Li+ BH3·SMe2 Camphor sulfonic acid Cl-CH2-OR Li°/NH3 Tf2O CuCN NIS Hydroxide, lithium NIS SiiPr3-OTf NaOMe Allyl-I Lutidine Bromoacetate Allyl-SnR3 BF3·OEt2 Zn° PdCl2(dppf) Alkynyl-Li DMPU (solvent) |