Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 21, Issue 5, Pages 950-954Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob02121h
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In this study, we report the [3,3]-sigmatropic rearrangement of in situ formed propargyl alkynyl ethers to allenyl ketenes, which leads to the formation of complex tert-butyl-(2E,4Z)-dienoates 2 with high yields upon tert-butanol addition. Similarly, the sigmatropic rearrangements of in situ formed propargyl lithioalkynyl ethers result in the formation of methyl-(2Z,4Z)-dienoates 4 upon methanol addition or unsaturated lactones 6 upon aldehyde or ketone addition.
In an extension of our studies on low-temperature rearrangements of 1-alkynyl ethers, we describe herein the [3,3]-sigmatropic rearrangement of in situ formed propargyl alkynyl ethers to allenyl ketenes, which furnish complex tert-butyl-(2E,4Z)-dienoates 2 in good yields upon tert-butanol addition. Similarly, sigmatropic rearrangements of in situ formed propargyl lithioalkynyl ethers yield methyl-(2Z,4Z)-dienoates 4 upon methanol addition or unsaturated lactones 6 upon aldehyde or ketone addition to the allenyl ynolate intermediate.
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