Cyclizations of α-Diketones to α-Hydroxycyclopentenones on Silica Gel in the Absence of Solvent
Elizabeth A. Uhrich, William A. Batson, Marcus A. Tius*
*2545 The Mall, University of Hawaii, Honolulu, HI 96822, USA, Email: tius
gold.chem.hawaii.edu
E. A. Uhrich, W. A. Batson, M. A. Tius, Synthesis, 2006, 2139-2142.
Abstract
Stirring α,β-unsaturated α-diketones in the presence of activated silica gel results in cyclization to α-hydroxycyclopentenones in good yield. The reaction is sensitive to the mode of stirring and proceeds more rapidly in the presence of triethylamine consistent with a Nazarov reaction proceeding through the enol tautomer.
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Key Words
diketones, cyclizations, Nazarov reaction, silica gel, rearrangements
ID: J66-Y2006-1990
