A direct phosphine-mediated synthesis of pyrroles from acid chlorides and alpha,beta-unsaturated imines.
A one-step method to assemble pyrroles from alpha,beta-unsaturated imines and acid chlorides has been developed. This reaction is mediated by triphenylphosphine, which eliminates phosphine oxide to allow cyclization. This reaction has been employed to access a diverse range of pyrroles via modulation of the two building blocks and applied as well to the synthesis of lukianol A.
Lu
Yingdong
Y
Department of Chemistry, McGill University, 801 Sherbrooke Street W., Montreal QC H3A 2K6, Canada.
Arndtsen
Bruce A
BA
D002712:Chlorides / Q000737:chemistry*; D003500:Cyclization; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D011720:Pyrazoles / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002712:Chlorides; D007097:Imines; D010720:Phosphines; D011720:Pyrazoles; D011758:Pyrroles; C116875:lukianol A; C044646:phosphine