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

Expédite Yen-Pon; Pier Alexandre Champagne; Lucie Plougastel; Sandra Gabillet; Pierre Thuéry; Mizuki Johnson; Gilles Muller; Grégory Pieters; Frédéric Taran; K. N. Houk; Davide Audisio

doi:10.1021/jacs.8b11465

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

Expédite Yen-Pon, Pier Alexandre Champagne, Lucie Plougastel, Sandra Gabillet, Pierre Thuéry, Mizuki Johnson, Gilles Muller, Grégory Pieters, Frédéric Taran, K. N. Houk, Davide Audisio

Research output: Contribution to journal › Article › peer-review

38 Scopus citations

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.

Original language	English (US)
Pages (from-to)	1435-1440
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	141
Issue number	4
DOIs	https://doi.org/10.1021/jacs.8b11465
State	Published - Jan 30 2019
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.8b11465

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

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.",

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doi = "10.1021/jacs.8b11465",

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AU - Yen-Pon, Expédite

AU - Champagne, Pier Alexandre

AU - Plougastel, Lucie

AU - Gabillet, Sandra

AU - Thuéry, Pierre

AU - Johnson, Mizuki

AU - Muller, Gilles

AU - Pieters, Grégory

AU - Taran, Frédéric

AU - Houk, K. N.

AU - Audisio, Davide

PY - 2019/1/30

Y1 - 2019/1/30

N2 - 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.

AB - 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.

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ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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