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DOI: 10.1055/a-2047-8456
Regioselective anti-Silyllithiation of Propargylic Amines
This work was supported by the Japan Society for the Promotion of Science (JSPS), KAKENHI (Grant nos. JP19F01033, JP19H00895, JP21H01934), and partly by the Japan Science and Technology Agency (JST), CREST (Grant no. JPMJCR19R4).
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Abstract
The regioselective anti-silyllithiation of propargylic amines is developed to facilitate the efficient synthesis of alkenylsilanes. This reaction generates an alkenyllithium intermediate that is stabilized by the formation of a five-membered cyclic structure through intramolecular coordination of the nitrogen functional group. Upon subsequent treatment with an electrophile, the alkenyllithium intermediate is further functionalized to afford tetrasubstituted allylic amines bearing a β-silicon substituent.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2047-8456.
- Supporting Information
Publication History
Received: 06 February 2023
Accepted after revision: 06 March 2023
Accepted Manuscript online:
06 March 2023
Article published online:
12 April 2023
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References and Notes
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