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• W3140187247 abstract "Generation of reactive intermediates and interception of these fleeting species in a cascade is a common strategy employed by Nature. However, formation of these species under mild conditions using traditional synthetic techniques can present a challenge. Here, we demonstrate the utility of biocatalysis in generating ortho-quinone methide intermediates under aqueous conditions and at reduced temperatures. Specifically, we applied an α-ketoglutarate-dependent non-heme iron enzyme, CitB, in the selective modification of benzylic C–H bonds of ortho-cresol substrates to afford a benzylic alcohol product which, under the reaction conditions, is in equilibrium with the corresponding ortho-quinone methide. Interception of the ortho-quinone methide by a nucleophile or a dienophile allows for one-pot conversion of benzylic C–H bonds into C–C, C–N, C–O, and C–S bonds in a chemoenzymatic cascade." @default.
• W3140187247 created "2021-04-13" @default.
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• W3140187247 date "2019-03-12" @default.
• W3140187247 modified "2023-09-29" @default.
• W3140187247 title "Biocatalyst-Initiated Ortho-Quinone Methide Formation and Derivatization" @default.
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• W3140187247 doi "https://doi.org/10.26434/chemrxiv.7828769.v1" @default.
• W3140187247 hasPublicationYear "2019" @default.
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