Synthesis of cyclopent-2-enones through stepwise [3 + 2] cycloaddition of simple silyl enol ethers and alk-1-ynes
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 22,p. 1708-1709
- https://doi.org/10.1039/c39930001708
Abstract
Treatment of silyl enol ethers and alk-1-ynes with SnCl4–Bu3N reagent followed by DBU, leads to cyclopent-2-enones, through [3 + 2] cycloaddition reactions; the initial carbon–carbon bond formation is carbometallation of alkynes, and the second step is a base-promoted intramolecular alkylation which reductively eliminates tin species (DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene).Keywords
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