PubAg

Main content area

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

Author:
Yen-Pon, Expédite, Champagne, Pier Alexandre, Plougastel, Lucie, Gabillet, Sandra, Thuéry, Pierre, Johnson, Mizuki, Muller, Gilles, Pieters, Grégory, Taran, Frédéric, Houk, K. N., Audisio, Davide
Source:
Journal of the American Chemical Society 2019 v.141 no.4 pp. 1435-1440
ISSN:
1520-5126
Subject:
cycloaddition reactions, regioselectivity
Abstract:
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.
Agid:
6288082