1618682-17-9Relevant academic research and scientific papers
3-Halotetrahydropyran-4-one derivatives from homopropargyl acetal
Aaseng, Jon Erik,Iqbal, Naseem,Tungen, Jorn Eivind,Sperger, Christian A.,Fiksdahl, Anne
, p. 2458 - 2467 (2014)
GRAPHICAL ABSTRACT A gold(I)-catalyzed regioselective method for the preparation of 3-bromo/iodo-tetrahydropyran-4-one derivatives from homopropargyl acetal is reported. A one-pot procedure based on a gold(I)-catalyzed Petasis-Ferrier rearrangement/cyclization and subsequent electrophilic halogenation was developed. Corresponding hemiacetals were not suitable substrates for the formation of the 3-halo-pyran derivatives. The present transformation is a useful method to readily afford highly substituted 3-halo-tetrahydropyran-4-ones, which are suitable substrates in a variety of reactions in further synthesis.
