| Reference: | Paquette, L. A.; Wiedeman, P. E.; Bulman-Page, P. C. J. Org. Chem. 1988, 53, 1441. DOI |
| Keywords: | CarboxEster -> Alkyl-OH • Acetoacetic ester synthesis • Alkyl-OH -> Aldehyde • Lactol -> Lactone • Acetal -> Aldehyde • Enone -> Ketal(thio) • Enone -> Ketal(thio) • Lactone enolate+Aldehyde • Dehydration -> EneLactone • Ketone+Mg-Alkynyl • CompE+-Ketone/CarboxEster+Mg-R • CompOx-Alkyl-OH/Sulfide+CrO3 • CompOx-Lactol/Alkyl-OH+CrO3 • Lactone-5 • Lactone enolate+Aldehyde • Reductive elimination - Se/OR • Lactone enolate+Alkyl-X • Deconjugative alkylation • Nazarov • Mechanism • |
| Reagents: | NaH • MeI • Alkynyl-MgX • HS-(CH2)2-SH • AlHiBu2 • TsOH • CrO3·Py2 (Collins) • CrO3, H2SO4 (Jones) • TsOH • HS-(CH2)2-SH • TsOH • TsOH • LiNiPr2 • Acetaldehyde • MeSO2Cl, NEt3 • DBU • LiNiPrCy • MeI • HMPA (solvent) • LiNiPr2 • MeI • LiNiPr2 • Phenylselenoacetaldehyde • MeSO2Cl, NEt3 • H2SO4 • |