Synthesis of highly substituted pyrroles via nucleophilic catalysis.
A nucleophilic catalysis method providing a concise synthesis of di-, tri-, and tetrasubstituted pyrroles is described. This regioselective one-pot method relies on nucleophilic catalysis of the intermolecular addition of oximes to activated alkynes and thermal rearrangement of the in situ generated O-vinyl oximes to form pyrroles that contain a functional group handle at the C3/C4 position.
Ngwerume
Simbarashe
S
School of Chemistry, University of Nottingham, Nottingham NG7 2RD, UK.
Camp
Jason E
JE
D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010091:Oximes / Q000737:chemistry; D010879:Piperazines / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C417980:4-(dimethylamine)pyridine; D000480:Alkynes; D009943:Organophosphorus Compounds; D010091:Oximes; D010879:Piperazines; D011725:Pyridines; D011758:Pyrroles; C061896:triphenylphosphine; C007306:triethylenediamine