T. Ren, Y. Liu, Q. Guo
Oct 1, 1996
Citations
0
Influential Citations
17
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
4-Methoxy-2,2,6,6-tetramethyl-1-oxopiperidinium chloride, made from the corresponding 1-piperidinyloxyl radical and chlorine gas, was used as an oxyfunctionalizing reagent for a number of enolizable ketones. Regioselective α- or γ-oxygenated carbonyl compounds were obtained smoothly at ambient temperature in moderate to good yields. Oxyfunctionalization of (+)-carvone and (−)-carvone proceeded stereoselectively, and provided cis-product (5R, 6S)- and (5S, 6R)-2-cyclohexen-1-ones, respectively. Interestingly, unsymmetrical ketones afforded isomeric α- and α′-oxygenated ketones, while allyl ketones gave the regiospecific γ-oxygenated products with the migration of the double bond in the allylic group.