ArticleAngewandte Chemie (International ed. in English)2022
Sigmatropic [1,5] Carbon Shift of Transient C3 Ammonium Enolates.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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Who cites it
2 citing papers in PubMed.
- Difluorocarbene-induced [1,2]- and [2,3]-Stevens rearrangement of tertiary amines.Nature communications · 2024Article
- Sigmatropic [1,5] Carbon Shift of Transient C3 Ammonium Enolates.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
4 authors.
Funding
Abstract
The stereospecific sigmatropic [1,5] carbon shift of C3 ammonium enolates is discovered. According to mechanistic, kinetic and computational experiments, this new rearrangement proceeds via the catalytic generation of a transient C3 ammonium enolate by intramolecular aza-Michael addition. This intermediate rapidly undergoes [1,5] sigmatropic carbon migration to furnish the respective tetrahydroquinoline-4-ones with excellent diastereoselectivities of d.r. >99 : 1 and in 61-98 % yield.
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