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Catalytic Enantio- and Regioselective Addition of Nucleophiles in the Intermolecular Hydrofunctionalization of 1,3-Dienes

https://doi.org/10.1021/acscatal.9b04712

Adamson, Nathan J.; Malcolmson, Steven J. (December 2019, ACS Catalysis)

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Enantioselective Construction of Quaternary Stereogenic Centers by the Addition of an Acyl Anion Equivalent to 1,3-Dienes

https://doi.org/10.1021/acs.orglett.0c00412

Adamson, Nathan J.; Park, Sangjune; Zhou, Pengfei; Nguyen, Andrew L.; Malcolmson, Steven J. (March 2020, Organic Letters)

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Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design

https://doi.org/10.1021/jacs.9b02637

Adamson, Nathan J.; Jeddi, Haleh; Malcolmson, Steven J. (May 2019, Journal of the American Chemical Society)

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Brønsted acid and Pd–PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes

https://doi.org/10.1039/c9sc00633h

Park, Sangjune; Adamson, Nathan J.; Malcolmson, Steven J. (May 2019, Chemical Science)

We describe the development of Pd–PHOX-catalysed enantioselective couplings of internal dienes with malononitrile and other activated C-pronucleophiles. Reactions are dramatically accelerated by the addition of Et 3 N·HBAr F 4 as a Brønsted acid co-catalyst, enabling a suite of products bearing a variety of alkyl substituents at the stereogenic carbon to be prepared. A series of mechanism-oriented experiments reveal key aspects of the catalytic cycle and the importance of the non-coordinating BAr F 4 counterion in not only promoting reactions of internal dienes but also additions of previously unreactive nucleophiles towards terminal dienes.
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