Sydnone-based Approach to Hetero-helicenes Through 1,3-Dipolar-Cycloadditions

Sydnone-based Approach to Hetero-helicenes Through 1,3-Dipolar-Cycloadditions

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

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 141; pp. 1435 - 1440
Main Authors: Yen-Pon, Expédite, Champagne, Pier Alexandre, Plougastel, Lucie, Gabillet, Sandra, Thuéry, Pierre, Johnson, Mizuki, Muller, Gilles, Pieters, Grégory, Taran, Frédéric, Houk, Kendall N, Audisio, Davide
Format: Journal Article
Language:English
Published: American Chemical Society 10-01-2019
Subjects:
Chemical Sciences
Organic chemistry
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Summary:The first approach to pyrazole containing helicenes via sydnone-aryne [3+2]-cycloaddition is described. An unprecedented regioselectivity in the cycloaddition step towards the more sterically constrained product was observed in presence of extended aromatic scaffolds. DFT calculations enabled to understand the origin of this unexpected selectivity.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b11465