Work

Michael Additions of Highly Basic Enolates toortho-Quinone Methides

Year: 2015

Type: article

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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5b00972

Authors: Robert S. Lewis, Christopher J. Garza, Ann T. Dang, Te Kie A. Pedro, William J. Chain

Institutions: University of Hawaiʻi at Mānoa, University of Hawaii Cancer Center

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Achievement Rewards for College Scientists Foundation, National Institutes of Health, University of California, Irvine, National Cancer Institute

Award: Carbonyls to Cancer Therapeutics