Switchable reactivity of acylated alpha, beta-dehydroamino ester in the Friedel-Crafts alkylation of indoles by changing the Lewis acid.
Highly regioselective electrophilic substitution of indoles with N-acetylated alpha,beta-dehydroalanine methyl ester, promoted by different transition metal salts was achieved. The orthogonal regioselectivity provides an efficient protocol toward highly functionalized 3-indolyl-alpha-amino acids. The mechanism of the reactions was explored by NMR studies.
Angelini
Elena
E
Institute of Medicinal Chemistry, University of Urbino Carlo Bo, Piazza del Rinascimento 6, 61029 Urbino (PU), Italy.
Balsamini
Cesarino
C
Bartoccini
Francesca
F
Lucarini
Simone
S
Piersanti
Giovanni
G
D000107:Acetylation; D000143:Acids / Q000737:chemistry*; D000215:Acylation; D000478:Alkylation; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure
D000143:Acids; D000588:Amines; D004952:Esters; D007211:Indoles; D006859:Hydrogen