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.
DOI: 10.1055/s-2006-942420
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.
see article for more examples
An Organocatalytic Asymmetric Nazarov Cyclization
A. K. Basak, N. Shimada, W. F. Bow, D. A. Vicic, M. A. Tius, J. Am. Chem. Soc., 2010, 132, 8266-8267.
Key Words
diketones, cyclizations, Nazarov reaction, silica gel, rearrangements
ID: J66-Y2006-1990
