Title: Substituent effects in tandem intramolecular silyl nitronate olefin cycloadditions (ISOC) leading to functionalized tetrahydrofurans
Authors: Hassner, A ×
Friedman, O
Dehaen, Wim #
Issue Date: Jan-1997
Publisher: Vch publishers inc
Series Title: Liebigs annalen-recueil issue:3 pages:587-594
Abstract: The intramolecular silyl nitronate olefin cycloaddition (ISOC) leading to substitued, fused-ring tetrahydrofurans 6 was examined with regard to optimum conditions and substituent effects. The required unsaturated nitro ethers 3 resulted from low-temperature, base-mediated Michael addition of allyl alcohols 2 to nitroolefins 1, followed by conversion to unsaturated silyl nitronates 4. Cycloaddition of the latter and elimination of silanol provided 6. One-pot tandem reactions, starting with nitroolefins 1 and allyl alcohols 2 and involving four steps, sometimes proceeded in better yields but often gave unexpected side products. Terminal olefinic electron-donating substituents (Me, MeO) increased the rate of cycloaddition, while an internal olefinic methyl substituent slowed down the reaction. In the case of nitronates possessing ester or nitrile moieties as terminal olefin substituents, tandem Michael addition to produce substituted furans 14, 15 occurred faster than trapping of the nitronate anion by TMSCl.
ISSN: 0947-3440
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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