Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions.

Expédite Yen-PonPier Alexandre ChampagneLucie PlougastelSandra GabilletPierre ThuéryMizuki JohnsonGilles MullerGrégory PietersFrédéric Taran Kendall N Houk Davide Audisio

Published in: Journal of the American Chemical Society (2019)

The first approach to pyrazole-containing helicenes via sydnone-aryne [3 + 2]-cycloaddition is described. An unprecedented regioselectivity in the cycloaddition step toward the more sterically constrained product was observed in the presence of extended aromatic scaffolds. DFT calculations enabled understanding the origin of this unexpected selectivity.

Keyphrases

density functional theory
molecular docking
molecular dynamics simulations
molecular dynamics
tissue engineering
amino acid
structural basis