4.7 Article

Regioselective side-chain amination of 2-alkyl azacycles by radical translocation: total synthesis of tetraponerine T8

Journal

CHEMICAL COMMUNICATIONS
Volume 57, Issue 7, Pages 919-922

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc07625b

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Funding

  1. EPSRC [EP/P016618/1, EP/N025652/1]
  2. EPSRC [EP/P016618/1, EP/N025652/1] Funding Source: UKRI

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This study reports a regioselective gamma-C-H amination method for the side-chain of saturated 2-alkyl nitrogen heterocycles, which proceeds through a sulfamide-directed 1,6-radical translocation. The practicality of this rapid access to 1,3-diamines is highlighted in a short synthesis of the alkaloid tetraponerine T8 and non-natural analogues.
The regioselective gamma-C-H amination of the side-chain of saturated 2-alkyl nitrogen heterocycles is reported, proceeding through a sulfamide-directed 1,6-radical translocation. The practicality of this rapid access to 1,3-diamines is highlighted in a short synthesis of the alkaloid tetraponerine T8 and non-natural analogues.

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