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Synfacts 2019; 15(04): 0363
DOI: 10.1055/s-0037-1612324
DOI: 10.1055/s-0037-1612324
Synthesis of Materials and Unnatural Products
A New Twist on Sydnones
Yen-Pon E,
Champagne PA,
Plougastel L,
Gabillet S,
Thuéry P,
Johnson M,
Muller G,
Pieters G,
Taran F,
Houk KN,
Audisio D.
* Université Paris-Saclary, Gif-sur-Yvette, France and University of California, Los Angeles, San José State University, USA
Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions.
J. Am. Chem. Soc. 2019;
141: 1435-1440
Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions.
J. Am. Chem. Soc. 2019;
141: 1435-1440
Further Information
Publication History
Publication Date:
19 March 2019 (online)
Significance
While helicenes have held the attention of chemists for years, expedient, selective syntheses to access such architectures are few and far between. In this report, Audisio and co-workers disclose a two-step method to a variety of pyrrazole-containing heterohelicenes through the cycloaddition of arynes and sydnones.
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Comment
To form the helical product selectively, it was found that the phenanthryne cycloaddition partner was key. The use of naphthyne and benzyne cycloaddition partners resulted in eroded selectivity. Computational studies revealed that a C–H···π interaction stabilized the transition state for the helicene.
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