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 Alkyl-X+Enolate Nazarov Mechanism |
Reagents: | NaH MeI Alkynyl-MgX Thiol, (CH2)2-SH AlHiBu2 TsOH CrO3·Py2 (Collins) CrO3, H2SO4 (Jones) TsOH Thiol, (CH2)2-SH TsOH TsOH LiNiPr2 Acetaldehyde Sulfonyl chloride, methane, NEt3 DBU LiNiPrCy MeI HMPA (solvent) LiNiPr2 MeI LiNiPr2 Phenylselenoacetaldehyde Sulfonyl chloride, methane, NEt3 H2SO4 |