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Copper-Catalyzed Diastereo-, Enantio-, and ( Z )-Selective Aminoallylation of Ketones through Reductive Couplings of Azatrienes for the Synthesis of Allylic 1,2-Amino Tertiary Alcohols

https://doi.org/10.1021/jacs.4c05637

Zhu, Jiaqi; Rahim, Faraan; Zhou, Pengfei; Zhang, Annie; Malcolmson, Steven J (July 2024, Journal of the American Chemical Society)

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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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Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes

https://doi.org/10.1021/acs.orglett.0c00342

Onyeagusi, Chibueze I.; Shao, Xinxin; Malcolmson, Steven J. (February 2020, Organic Letters)

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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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Development and Mechanistic Investigations of Enantioselective Pd-Catalyzed Intermolecular Hydroaminations of Internal Dienes

https://doi.org/10.1021/acscatal.8b01914

Park, Sangjune; Malcolmson, Steven J. (August 2018, ACS Catalysis)

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Rational ligand choice extends the SABRE substrate scope

https://doi.org/10.1039/d0cc01330g

Colell, Johannes F.; Logan, Angus W.; Zhou, Zijian; Lindale, Jacob R.; Laasner, Raul; Shchepin, Roman V.; Chekmenev, Eduard Y.; Blum, Volker; Warren, Warren S.; Malcolmson, Steven J.; et al (January 2020, Chemical Communications)

Here we report on chelating ligands for Signal Amplification By Reversible Exchange (SABRE) catalysts that permit hyperpolarisation on otherwise sterically hindered substrates. We demonstrate 1 H enhancements of ∼100-fold over 8.5 T thermal for 2-substituted pyridines, and smaller, yet significant enhancements for provitamin B 6 and caffeine. We also show 15 N-enhancements of ∼1000-fold and 19 F-enhancements of 30-fold.
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