Tetrahedron letters

A convenient deoxygenation of α, β-epoxy ketones to enones

RB dos Santos, TJ Brocksom, U Brocksom

Index: Dos Santos, Reginaldo B.; Brocksom, Timothy John; Brocksom, Ursula Tetrahedron Letters, 1997 , vol. 38, # 5 p. 745 - 748

Full Text: HTML

Citation Number: 24

Abstract

A new and efficient methodology for the deoxygenation of α, β-epoxy ketones to enones has been developed, using aminoiminomethanesulfinic acid (thiourea dioxide) as the reducing agent under phase transfer conditions. The epoxides of mesityl oxide, isophorone,(−)- carvone,(+)-6-methyl-carvone,(+)-6-ethyl-carvone and (−)-myrtenal, were converted into their respectives enones in good to excellent yields.

Related Articles:

Nanosized sulfated zinc ferrite as catalyst for the synthesis of nopol and other fine chemicals

[Catalysis Today, , vol. 198, # 1 p. 98 - 105]

A one-pot conversion of olefins to. alpha.,. beta.-unsaturated carbonyl compounds. An easy synthesis of 2-cyclopentenone and related compounds

[Mihelich, Edward D.; Eickhoff, David J. Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 4135 - 4137]

Hydroboration. 90. Synthesis of 2-Isobutyl-and 2-Isopropylapopinenes. Rates and Stoichiometry of the Hydroboration of 2-Organylapopinenes with Borane-Methyl …

[Journal of Organic Chemistry, , vol. 59, # 8 p. 2025 - 2032]

Hydroxylation by cytochrome P-450 and metalloporphyrin models. Evidence for allylic rearrangement

[Journal of the American Chemical Society, , vol. 106, # 7 p. 2177 - 2181]

More Articles...