1,3-Aza-Brook Rearrangement of Aniline Derivatives: In Situ Generation of 3-Aminoaryne via 1,3-C-(sp2)-to-N Silyl Migration
In: Organic Letters, Jg. 23 (2021-09-23), S. 7545-7549
Online
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Zugriff:
The design, synthesis, and validation of 3-aminobenzyne precursors induced by C-(sp2)-to-N 1,3-aza-Brook rearrangement have been achieved, allowing access to diverse aniline derivatives. Through crossover experiments, we demonstrated the intramolecular mechanism of 1,3-C-to-N silyl transfer. To gain insight into the regioselectivity observed in the reactions, we performed density functional theory calculations. Finally, the method was applied to the synthesis of xylanigripones A in five linear steps in an overall yield of 30%.
Titel: |
1,3-Aza-Brook Rearrangement of Aniline Derivatives: In Situ Generation of 3-Aminoaryne via 1,3-C-(sp2)-to-N Silyl Migration
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Autor/in / Beteiligte Person: | Jeon, Young-Kyo ; Kim, Won-Suk |
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Zeitschrift: | Organic Letters, Jg. 23 (2021-09-23), S. 7545-7549 |
Veröffentlichung: | American Chemical Society (ACS), 2021 |
Medientyp: | unknown |
ISSN: | 1523-7052 (print) ; 1523-7060 (print) |
DOI: | 10.1021/acs.orglett.1c02751 |
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