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A Straightforward Route to Helically Chiral N‐Heteroaromatic Compounds: Practical Synthesis of Racemic 1,14‐Diaza[5]helicene and Optically Pure 1‐ and 2‐Aza[6]helicenes
Abstract
The taming of the screw: The CoI-catalyzed cyclotrimerization of triynes and microwave (MW) assisted aromatization with MnO2 are central to the practical synthesis of diaza[5]helicene and aza[6]helicenes. The aza[6]helicene racemates have been resolved, the absolute configuration of the enantiomers assigned, the energy barriers to racemization determined, and X-ray structures of their Ag complexes obtained (see picture; Cp=C5H5, OTf=triflate).
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Cited by
One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes
Gingras, M. (2013) · Chem. Soc. Rev. · doi:10.1039/c2cs35154d · Cited by 802
Matsumoto, A., Yonemitsu, K., Ozaki, H., Míšek, J., Starý, I., Stará, I. G., & Soai, K. (2017) · Organic & Biomolecular Chemistry · doi:10.1039/c6ob02745h · Cited by 45
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Metadata
- Authors
- Míšek, J., Teplý, F., Stará, I. G., Tichý, M., Šaman, D., Císařová, I., Vojtíšek, P., & Starý, I.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2008-04-08
- Volume
- 47
- Issue
- 17
- Pages
- 3188-3191
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2149608722
- Cited by
- 175
- References
- 0
- FWCI
- 9.24
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: A Straightforward Route to Helically Chiral N‐Heteroaromatic Compounds: Practical Synthesis of Racemic 1,14‐Diaza[5]helicene and Optically Pure 1‐ and 2‐Aza[6]helicenes. https://app.cochat.ai/papers/10.1002/anie.200705463
- The paper
- Míšek, J., Teplý, F., Stará, I. G., Tichý, M., Šaman, D., Císařová, I., Vojtíšek, P., & Starý, I. (2008). A Straightforward Route to Helically Chiral N‐Heteroaromatic Compounds: Practical Synthesis of Racemic 1,14‐Diaza[5]helicene and Optically Pure 1‐ and 2‐Aza[6]helicenes. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.200705463
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