Ring closure to beta-turn mimics via copper-catalyzed azide/alkyne cycloadditions.
[Structure: see text]. Copper-catalyzed azide alkyne cycloadditions of the linear substrates 1 were used to form the cyclic derivatives 2. Computational, NMR, and CD analyses of these compounds indicate that their most favorable conformational states include type I and type II beta-turn conformations. Selectivity for the dimeric products 6 in these cyclization reactions is discussed.
Angell
Yu
Y
Chemistry Department, Texas A & M University, P.O. Box 30012, College Station, Texas 77842, USA.
Burgess
Kevin
K
D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D002942:Circular Dichroism; D003198:Computer Simulation; D003300:Copper / Q000494:pharmacology*; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D018716:Molecular Mimicry; D015394:Molecular Structure
D000480:Alkynes; D001386:Azides; D003300:Copper