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Iridium-Catalyzed Allylic Amination Route to ?-Aminoboronates: Illustration of the Decisive Role of Boron Substituents.

ABSTRACT: The development of a new route to ?-aminoboronates using an iridium-catalyzed allylic amination on boronated substrates is described. Unlike the boronate group, the trifluoroborato substituent was found to govern the regioselectivity exclusively in favor of branched products. The transformation of an allylic substitution product into an ?-aminoboronic ester in an efficient way validated the implementation of this approach.

SUBMITTER: Touchet S

PROVIDER: S-EPMC3281748 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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Iridium-Catalyzed Allylic Amination Route to α-Aminoboronates: Illustration of the Decisive Role of Boron Substituents.

Touchet Sabrina S Carreaux François F Molander Gary A GA Carboni Bertrand B Bouillon Alexandre A

Advanced synthesis & catalysis 20111201 18

The development of a new route to α-aminoboronates using an iridium-catalyzed allylic amination on boronated substrates is described. Unlike the boronate group, the trifluoroborato substituent was found to govern the regioselectivity exclusively in favor of branched products. The transformation of an allylic substitution product into an α-aminoboronic ester in an efficient way validated the implementation of this approach. ...[more]

PMID: 22350584

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