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Synthesis of Unsymmetrical Vicinal Diamines via Directed Hydroamination.


ABSTRACT: Vicinal diamines are a common motif found in biologically active molecules. The hydroamination of allyl amine derivatives is a powerful approach for the synthesis of substituted 1,2-diamines. Herein, the rhodium-catalyzed hydroamination of primary and secondary allylic amines using diverse amine nucleophiles, including primary, secondary, acyclic, and cyclic aliphatic amines to access a wide range of unsymmetrical vicinal diamines, is presented. The utility of this methodology is further demonstrated through the rapid synthesis of several bioactive molecules and analogs.

SUBMITTER: Lee BJ 

PROVIDER: S-EPMC9757009 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Synthesis of Unsymmetrical Vicinal Diamines via Directed Hydroamination.

Lee Byung Joo BJ   Ickes Andrew R AR   Gupta Anil K AK   Ensign Seth C SC   Ho Tam D TD   Tarasewicz Anika A   Vanable Evan P EP   Kortman Gregory D GD   Hull Kami L KL  

Organic letters 20220721 30


Vicinal diamines are a common motif found in biologically active molecules. The hydroamination of allyl amine derivatives is a powerful approach for the synthesis of substituted 1,2-diamines. Herein, the rhodium-catalyzed hydroamination of primary and secondary allylic amines using diverse amine nucleophiles, including primary, secondary, acyclic, and cyclic aliphatic amines to access a wide range of unsymmetrical vicinal diamines, is presented. The utility of this methodology is further demonst  ...[more]

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