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

Authors :
Yen-Pon E
Champagne PA
Plougastel L
Gabillet S
Thuéry P
Johnson M
Muller G
Pieters G
Taran F
Houk KN
Audisio D
Source :
Journal of the American Chemical Society [J Am Chem Soc] 2019 Jan 30; Vol. 141 (4), pp. 1435-1440. Date of Electronic Publication: 2019 Jan 15.
Publication Year :
2019

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.

Details

Language :
English
ISSN :
1520-5126
Volume :
141
Issue :
4
Database :
MEDLINE
Journal :
Journal of the American Chemical Society
Publication Type :
Academic Journal
Accession number :
30628450
Full Text :
https://doi.org/10.1021/jacs.8b11465