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  • Palladium-catalyzed intramolecular diamination of acrylic esters using sulfamates as nitrogen source.

Palladium-catalyzed intramolecular diamination of acrylic esters using sulfamates as nitrogen source.

The Journal of organic chemistry (2012-01-31)
Patricia Chávez, Jonathan Kirsch, Jan Streuff, Kilian Muñiz
ABSTRACT

An intramolecular diamination of acrylates is reported using sulfamates as nitrogen sources. This reaction proceeds under palladium(II) catalysis with copper bromide as oxidant and gives rise to anti-configured 2,3-diamino carboxylates as bicyclic sulfamate derivatives. An aminobrominated intermediate within the diamination reaction was isolated that allowed to clarify the reaction mechanism and to rationalize the observed preferential product stereochemistry.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Sulfamic acid, 99.999% trace metals basis
Supelco
Sulfamic acid, analytical standard (for acidimetry), ACS reagent
Sigma-Aldrich
Sulfamic acid, ≥99.5% (alkalimetric)
Sigma-Aldrich
Ammonium sulfamate, ACS reagent, ≥98.0%
Sigma-Aldrich
Sulfamic acid, ReagentPlus®, ≥99%
Sigma-Aldrich
Sulfamic acid, ACS reagent, 99.3%
Sigma-Aldrich
Sulfamic acid, reagent grade, 98%
Sigma-Aldrich
Ammonium sulfamate, BioXtra, ≥98.0%