LIC-KOR-promoted synthesis of alkoxydienyl amines: an entry to 2,3,4,5-tetrasubstituted pyrroles.
A stereoselective approach to the synthesis of (E)-alkoxydienylamines (2) is described, starting from alpha,beta-unsaturated acetals (1) and aryl imines, under superbasic conditions. These can be readily converted into alpha-arylglycine derivatives (3) by mild acidic hydrolysis or, in turn, cyclized under oxidative conditions in the presence of a Pd catalyst to 2,3,4,5-tetrasubstituted pyrroles (4).
Blangetti
Marco
M
Dipartimento di Chimica Generale e Chimica Organica, Universita di Torino, Via P. Giuria 7, 10125 Torino, Italy.
Deagostino
Annamaria
A
Prandi
Cristina
C
Tabasso
Silvia
S
Venturello
Paolo
P
D000080:Acetals / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000080:Acetals; D000588:Amines; D007097:Imines; D011758:Pyrroles; D010165:Palladium; D005998:Glycine