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 → Enol-R 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 EnolEther → Acetal |
Reagents: | Oxetane CrO3Cl·PyH (PCC) P(O)(OCH2CF3)2CHR-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 Sulfonyl chloride, methane, NEt3 BH4-Na+ Allenyl-Li Fluoride, R4N+ BuLi(sec) HF·Py 18-cr-6 DMSO (solvent) HMPA (solvent) SnCl4 Fluoride, R4N+ HF·Py BF3·OEt2 |