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.

Michael Additions of Highly Basic Enolates to ortho-Quinone Methides. -Ketone and ester enolates are transformed with ortho-quinone methides generated in situ from silylated precursors. Depending on the substrates used, the reaction provides either -(2-hydroxyphenyl)carbonyl compounds or diastereomeric mixtures of the corresponding cyclic ketals or, rarely, mixtures of the two products. -(LEWIS, R. S.; GARZA, C. J.; DANG, A. T.; PEDRO, T. K. A.; CHAIN*, W. J.; Org. Lett. 17 (2015) 9, 2278-2281, http://dx.doi.org/10.1021/acs.orglett.5b00972 ; Dep. Chem., Univ. Hawaii, Honolulu, HI 96822, USA; Eng.) -F. Schill 37-165