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

The regioselective γ-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 a...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-01, Vol.57 (7), p.919-922
Main Authors: Griggs, Samuel D, Martin-Roncero, Alejandro, Nelson, Adam, Marsden, Stephen P
Format: Article
Language:English
Subjects:
Chains
Crystallography
Diamines
Regioselectivity
Synthesis
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Summary:The regioselective γ-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. Radical translocation facilitates the regioselective γ-amination of 2-alkyl-substituted azacycles, leading to 1,3-diamines including the alkaloidal natural product tetraponerine T8.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc07625b