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

Nathan J. Adamson, Haleh Jeddi, Steven J. Malcolmson*

*Department of Chemistry, Duke University, Durham, North Carolina 27708, United States, Email: steven.malcolmsonduke.edu

N. J. Adamson, H. Jeddi, S. J. Malcolmson, J. Am. Chem. Soc., 2019, 141, 8574-8583.

DOI: 10.1021/jacs.9b02637 (free Supporting Information)


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Abstract

Conjugated enynes undergo selective 1,4-hydroamination under Pd catalysis to deliver chiral allenes with pendant allylic amines. Several primary and secondary aliphatic and aryl-substituted amines couple with a wide range of mono- and disubstituted enynes in a nonenantioselective reaction where DPEphos serves as the ligand. Benzophenone can be used as an ammonia surrogate.

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Key Words

allenes, allylic amines


ID: J48-Y2019