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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:

E. A. Uhrich, W. A. Batson, M. A. Tius, Synthesis, 2006, 2139-2142.

DOI: 10.1055/s-2006-942420


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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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