4.8 Article

Copper(II) carboxylate promoted intramolecular diamination of terminal alkenes: Improved reaction conditions and expanded substrate scope

Journal

ORGANIC LETTERS
Volume 9, Issue 10, Pages 2035-2038

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol0706713

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Funding

  1. NIGMS NIH HHS [R01 GM078383-01, R01 GM078383, R01 GM07838301] Funding Source: Medline

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The copper(II) carboxylate promoted diamination reaction has been improved by the use of the organic soluble copper(II) neodecanoate [Cu( ND)(2)]. Cu(ND)(2) allowed the less-polar solvent dichloroethane (DCE) to be used, and as a consequence, decomposition of less-reactive substrates could be avoided. High diastereoselectivity was observed in the synthesis of 2,5-disubstituted pyrrolidines. Ureas, bis(anilines), and alpha-amido pyrroles derived from 2-allylaniline could also participate in the diamination reaction.

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