Synthesis of Unsymmetrical Vicinal Diamines via Directed Hydroamination.

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.

Citation

Byung Joo Lee, Andrew R Ickes, Anil K Gupta, Seth C Ensign, Tam D Ho, Anika Tarasewicz, Evan P Vanable, Gregory D Kortman, Kami L Hull. Synthesis of Unsymmetrical Vicinal Diamines via Directed Hydroamination. Organic letters. 2022 Aug 05;24(30):5513-5518

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PMID: 35862860

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