| Reference: | Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248. DOI |
| Keywords: | Alkyl-OH -> Aldehyde EnoateEster -> Allyl-OH Epoxide -> Chlorohydrin O-H -> O-SO2R Alkyl-OH -> Aldehyde Aldehyde -> Enolsilane Aldehyde -> Enal Saegusa oxidation Alkyl-X -> Alkyl-CN CompE+-Alkyl-X/Alkyl-X+NaCN Enal -> Allyl-OH O-H -> O-SO2R Si-Alkynyl -> H-Alkynyl HWE -> EnoateEster-cis Peterson -> Enyne Li-Allenyl/Propargyl+Aldehyde Aldehyde+Li-R Nitrile -> Aldehyde Li-Vinyl+Oxetane Si-Vinyl -> H-Vinyl Saegusa oxidation Aldehyde -> Enal Enolsilane -> Enal Allyl-OR -> Allyl-H Sharpless epoxidation O-SiPh2tBu -> O-H Si-Vinyl+Acetal Ether-8 |
| Reagents: | BF3·OEt2 CrO3Cl·PyH (PCC) P(O)(OCH2CF3)2CH2-CO2Me KN(SiMe3)2 AlHiBu2 Epoxide Ti(OiPr)4 TsCl, Py Vinyl-OR TsOH·Py CrO3Cl·PyH (PCC) NHiPr2 Pd(OAc)2 Cyanide, sodium AlHiBu2 AlHiBu2 MeSO2Cl, NEt3 BH4-Na+ Allenyl-Li Fluoride, Bu4N+ BuLi(sec) HF·Py 18-cr-6 DMSO (solvent) HMPA (solvent) SnCl4 Fluoride, Bu4N+ HF·Py |