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Synthesis of Chiral Triamine Ligands from Ephedrine and Pseudoephedrine
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1990
Year
Substitution ReactionDiversity Oriented SynthesisEngineering1,2-Diphenyl-3,4,7-trimethyl-1,4,7-triazaoctanes 1Natural SciencesDiversity-oriented SynthesisCarbinol Stereogenic CenterOrganic ChemistryStereoselective SynthesisChemistryPharmacologyChiral Triamine LigandsSynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringNatural Product Synthesis
Ephedrine (2) and pseudoephedrine (3) can be alkylated with α-chloro-N,N-dimethylacetamide and converted regio- and stereospecifically into 1,2-diphenyl-3,4,7-trimethyl-1,4,7-triazaoctanes 1 and 6 via a substitution reaction at the carbinol stereogenic center.