4.8 Article

Synthesis of Unsymmetrical Vicinal Diamines via Directed Hydroamination

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ORGANIC LETTERS
卷 24, 期 30, 页码 5513-5518

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01911

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资金

  1. NIH [R35 GM125029]
  2. Sloan Foundation [FG-2016-6568]
  3. Welch Foundation [FG- 2016-6568]
  4. Amgen
  5. Novartis
  6. University of Illinois, Urbana - Champaign
  7. University of Texas at Austin
  8. Bristol-Myers Squibb and Pines Graduate Fellowships
  9. Eli Lilly

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In this study, the rhodium-catalyzed hydroamination of allyl amine derivatives using various amine nucleophiles was presented. This methodology provides a powerful approach for the synthesis of unsymmetrical vicinal diamines and has been demonstrated to be useful in the rapid synthesis of bioactive molecules and analogs.
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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