title: Michael Additions of Highly Basic Enolates to ortho-Quinone Methides.
abstract: A protocol by which ketone or ester enolates and ortho-quinone methides (o-QMs) are generated in situ in a single reaction flask from silylated precursors under the action of anhydrous fluoride is reported. The reaction partners are joined to give a variety of β-(2-hydroxyphenyl)-carbonyl compounds in 32-94% yield in a single laboratory operation. The intermediacy of o-QMs is supported by control experiments utilizing enolate precursors and conventional alkyl halides as competitive alkylating agents and the isolation of 1,5-dicarbonyl products resulting from conjugate additions that do not restore the aromatic system.
authors.affiliation: †Department of Chemistry, University of Hawaii at Manoa, 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States.
authors.forename: Robert S
authors.initials: RS
authors.lastname: Lewis
authors.affiliation: †Department of Chemistry, University of Hawaii at Manoa, 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States.
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Garza
authors.affiliation: †Department of Chemistry, University of Hawaii at Manoa, 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States.
authors.forename: Ann T
authors.initials: AT
authors.lastname: Dang
authors.affiliation: †Department of Chemistry, University of Hawaii at Manoa, 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States.
authors.forename: Te Kie A
authors.initials: TK
authors.lastname: Pedro
authors.affiliation: †Department of Chemistry, University of Hawaii at Manoa, 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States.|‡The University of Hawaii Cancer Center, 701 Ilalo Street, Honolulu, Hawaii 96813, United States.
authors.forename: William J
authors.initials: WJ
authors.lastname: Chain
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D004952:Esters; D045563:Indolequinones / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002264:Carboxylic Acids; D004952:Esters; D045563:Indolequinones; D007659:Ketones; C068040:quinone methide