Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes

26 August 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Unprotected keto- and aldoximes are readily C-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly-substituted N-alpha-secondary (2°) and tertiary (3°) hydroxylamines. The method’s synthetic utility is demonstrated with the total synthesis of the trace alkaloid N-methyl-euphococcine. Preliminary experimental and computational mechanistic studies point toward the formation of a boroxine as the active allylating species.


boronic acids
homotropane alkaloids


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