Issue 7, 2021

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

Abstract

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
20 Nov. 2020
Accepted
18 Dec. 2020
First published
18 Dec. 2020

Chem. Commun., 2021,57, 919-922

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

S. D. Griggs, A. Martin-Roncero, A. Nelson and S. P. Marsden, Chem. Commun., 2021, 57, 919 DOI: 10.1039/D0CC07625B

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