Oxidative 1,4-Diamination of Dienes Using Simple Urea Derivatives

Diamination of alkenes and dienes has found widespread use in the synthesis of biologically active target molecules. Although the 1,2-diamination of alkenes has been comprehensively explored, versatile methods that install higher order 1,n-diamine moieties (e.g., n = 3–5) are not broadly developed....

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Bibliographic Details
Published in:Organic letters 2014-10, Vol.16 (19), p.5112-5115
Main Authors: Anumandla, Devendar, Littlefield, Ryan, Jeffrey, Christopher S
Format: Article
Language:English
Subjects:
Catalysis
Diamines - chemistry
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Molecular Structure
Oxidation-Reduction
Urea - analogs & derivatives
Urea - chemistry
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Summary:Diamination of alkenes and dienes has found widespread use in the synthesis of biologically active target molecules. Although the 1,2-diamination of alkenes has been comprehensively explored, versatile methods that install higher order 1,n-diamine moieties (e.g., n = 3–5) are not broadly developed. Herein, we report the development of an oxidative 1,4-diamination of dienes. This method represents one of the scarce examples of exclusive regioselectivity for 1,4-diamination. The reaction is easy to perform, uses simple reagents, works with a variety of functionalized dienes, and provides unique heterocyclic products.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502460j