A convenient deoxygenation of α,β-epoxy ketones to enones
✍ Scribed by Reginaldo B. dos Santos; Timothy John Brocksom; Ursula Brocksom
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 164 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A new and efficient methodology for the deoxygenation of ct,13-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 (-)-rnyrtenal, were converted into their respectives enones in good to excellent yields.
📜 SIMILAR VOLUMES
Deoxygenation of a,b-epoxy ketones and a,b-epoxy esters is accomplished in high yields under mild and neutral conditions by the use of Mo(CO) 6 .
In connection with studies on the total synthesis of the aglycone of erythromycin B, erythronolide B (II), it was of interest to devise a method for the conversion of the cu,@-unsaturated ketone I to II. The ketone I is an especially attractive synthetic intermediate for several reasons including ac