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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 ?-(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.

SUBMITTER: Lewis RS 

PROVIDER: S-EPMC4500648 | biostudies-literature | 2015 May

REPOSITORIES: biostudies-literature

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

Lewis Robert S RS   Garza Christopher J CJ   Dang Ann T AT   Pedro Te Kie A TK   Chain William J WJ  

Organic letters 20150423 9

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 ag  ...[more]

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