Aryl annulation of cyclic ketones via a magnesium carbometalation-6-pi- electrocyclization protocol |
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| Authors: | Tessier Pierre E Nguyen Natalie Clay Matthew D Fallis Alex G |
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| Affiliation: | Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5. |
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| Abstract: | A new strategy for the aryl annulation of cyclic ketones is described. Palladium(0) coupling of a propargyl alcohol with the enol triflate of a ketone and addition of vinylmagnesium chloride generates a triene as a magnesium chelate that may be quenched with an electrophile. In some cases, the triene cyclizes under the reaction conditions. Aromatization is accomplished by exposure to manganese dioxide or dichlorodicyanoquinone (DDQ). [reaction: see text] |
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