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Merck
CN

Oxidative 1,4-diamination of dienes using simple urea derivatives.

Organic letters (2014-09-13)
Devendar Anumandla, Ryan Littlefield, Christopher S Jeffrey
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Urea solution, 40 % (w/v) in H2O
Sigma-Aldrich
Urea solution, BioUltra, ~8 M in H2O
Sigma-Aldrich
Urea-12C, 99.9 atom % 12C
Millipore
Urea solution, suitable for microbiology, 40% in H2O
USP
Urea, United States Pharmacopeia (USP) Reference Standard
Urea, European Pharmacopoeia (EP) Reference Standard
Supelco
Urea, 8 M (after reconstitution with 16 mL high purity water)
Supelco
Urea, analytical standard
Sigma-Aldrich
Urea, puriss., meets analytical specification of Ph. Eur., BP, USP, 99.0-100.5%, 99.0-101.0% (calc. on dry substance)
Sigma-Aldrich
Urea, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99%
Sigma-Aldrich
Urea, BioXtra, pH 7.5-9.5 (20 °C, 5 M in H2O)
Sigma-Aldrich
Urea, suitable for electrophoresis
Sigma-Aldrich
Urea, ReagentPlus®, ≥99.5%, pellets
Sigma-Aldrich
Urea, ACS reagent, 99.0-100.5%
Sigma-Aldrich
Urea, BioUltra, Molecular Biology, 99% (T)
Sigma-Aldrich
Urea, powder, BioReagent, Molecular Biology, suitable for cell culture
Sigma-Aldrich
Urea, Vetec, reagent grade, 99%
Sigma-Aldrich
Urea, meets USP testing specifications