Direct preparation of substituted olefins from epoxides utilizing lithium tetraalkylcerate
✍ Scribed by Yutaka Ukaji; Tamotsu Fujisawa
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 246 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Alkylated olefins were directly synthesized in good yields by the deoxygenation reaction of epoxides with concomitant introduction of the alkyl group using lithium tetraalkylcerate. Styreneoxide and (I-naphthyl)ethyleneoxide gave terminal olefins, while ethyleneoxide replaced by aliphatic substituent, 1,2-epoxy-4-phenylbutane, afforded internal olefin. The utility of the present method was demonstrated in the one-step synthesis of a sesquiterpene, dehydro-a-curcumene.
Epoxide is one of the most useful compounds in organic synthesis depending on its great availability, and is used as a valuable precursor to olefin, alcohol, and carbonyl compound.l Among lots of reactions of epoxides, deoxy-