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ID 117097
Author
Yamasaki, Kohta Tokushima University
Yamauchi, Akiho Tokushima University
Miyakawa, Yasunori Kyoto University
Wang, Yinli Tokushima University|Kyoto University
Oriez, Raphaël Kyoto University
Yamaoka, Yousuke Kyoto University
Takasu, Kiyosei Kyoto University
Content Type
Journal Article
Description
We previously reported an intramolecular migrative cyclization of propargylsufones and sulfonylalkynamides giving oxa- and azacycles, respectively. To confirm the postulated reaction mechanism, the reaction was conducted with chiral nucleophiles such as N-heterocyclic carbenes, phosphines, and pyridines, or with sulfinate anions and chiral cations. As expected, migrative cyclization proceeded to give the enantiomerically enriched products. These results strongly support the postulated mechanism and provide the first example of the asymmetric version of this reaction.
Journal Title
Asian Journal of Organic Chemistry
ISSN
21935815
Publisher
Wiley-VCH|Asian Chemical Editorial Society
Volume
10
Issue
7
Start Page
1828
End Page
1834
Published Date
2021-04-16
Rights
This is the peer reviewed version of the following article: K. Yamasaki, A. Yamauchi, T. Inokuma, Y. Miyakawa, Y. Wang, R. Oriez, Y. Yamaoka, K. Takasu, N. Tanaka, Y. Kashiwada, K.-i. Yamada, Asian J. Org. Chem. 2021, 10, 1828., which has been published in final form at https://doi.org/10.1002/ajoc.202100274. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
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language
eng
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departments
Pharmaceutical Sciences
Bioscience and Bioindustry