Enyne metathesis-oxidation sequence for the synthesis of 2-phosphono pyrroles: proof of the "yne-then-ene" pathway.
A new tandem reaction sequence has been developed for the synthesis of 2-phosphono pyrroles. The sequence consists of ring-closing enyne metathesis of a substituted aminophosphonate, containing a terminal alkyne and an internal alkene, in combination with in situ oxidation of the produced 3-pyrrolines using tetrachloroquinone. By analyzing the formation of the end and certain byproducts, taking into account the difference in reactivity of different substrates and carefully studying spectroscopic data, it was found that the reaction proceeds by means of the "yne-then-ene" pathway. During the initiation phase, a new ruthenium carbene is formed which continues the propagation cycle.
Dieltiens
Nicolai
N
Research Group SynBioC, Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, 9000 Ghent, Belgium.
Moonen
Kristof
K
Stevens
Christian V
CV
D000588:Amines / Q000737:chemistry; D002384:Catalysis; D006838:Hydrocarbons / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010758:Phosphorus / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*; D013057:Spectrum Analysis
D000588:Amines; D006838:Hydrocarbons; D011758:Pyrroles; C030011:carbene; D010758:Phosphorus; D008697:Methane