Literature DB >> 25906358

Michael Additions of Highly Basic Enolates to ortho-Quinone Methides.

Robert S Lewis1, Christopher J Garza1, Ann T Dang1, Te Kie A Pedro1, William J Chain1,2.   

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.

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Year:  2015        PMID： 25906358      PMCID： PMC4500648          DOI： 10.1021/acs.orglett.5b00972

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  15 in total

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