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. 2022 Aug 5;24(30):5513-5518.
doi: 10.1021/acs.orglett.2c01911. Epub 2022 Jul 21.

Synthesis of Unsymmetrical Vicinal Diamines via Directed Hydroamination

Byung Joo Lee  1 , Andrew R Ickes  2 , Anil K Gupta  2 , Seth C Ensign  2 , Tam D Ho  1 , Anika Tarasewicz  1 , Evan P Vanable  3 , Gregory D Kortman  1 , Kami L Hull  1   2
Affiliations

Synthesis of Unsymmetrical Vicinal Diamines via Directed Hydroamination

Byung Joo Lee et al. Org Lett. .

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.

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Figures

Figure 1.
Figure 1.
Bioactive molecules containing 1,2-diamines and the proposed hydroamination reaction.
Scheme 1.
Scheme 1.
Synthetic Application
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