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Applications of ortho -Quinone Methide Intermediates in Catalysis and Asymmetric Synthesis

2011; American Chemical Society; Volume: 76; Issue: 22 Linguagem: Inglês

10.1021/jo201789k

1520-6904

Tejas P. Pathak, Matthew S. Sigman,

Multicomponent Synthesis of Heterocycles

Ortho-quinone methides are important synthetic intermediates and widely implicated in biological processes. In this Synopsis, recent advances concerning the synthesis and utility of these intermediates are discussed with a particular emphasis on metal-catalyzed formation of quinone methide intermediates. Additionally, applications of these intermediates as partners in asymmetric synthesis will be discussed including methods we have developed that involve the enantioselective Pd-catalyzed formation of ortho-quinone methides and the trapping of aforementioned intermediates with diverse nucleophiles.