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 nuc...

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Published inOrganic letters Vol. 24; no. 30; pp. 5513 - 5518
Main Authors Lee, Byung Joo, Ickes, Andrew R., Gupta, Anil K., Ensign, Seth C., Ho, Tam D., Tarasewicz, Anika, Vanable, Evan P., Kortman, Gregory D., Hull, Kami L.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.08.2022
Amer Chemical Soc
Subjects
Amines
Catalysis
Chemistry
Chemistry, Organic
Diamines
Physical Sciences
Rhodium
Science & Technology
Stereoisomerism
DRUG
ALKENES
MECHANISM
DIAMINATION
DIAZIDATION
THERAPEUTIC-USE
DISCOVERY
PHARMACOLOGICAL-PROPERTIES
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Summary: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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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.2c01911