Rhodium-catalyzed dynamic kinetic resolution of racemic internal allenes towards chiral allylated triazoles and tetrazoles
Abstract: A general Rh-catalyzed addition reaction of nitrogen containing heterocycles to internal allenes is reported. Starting from racemic internal allenes a dynamic kinetic resolution (DKR) provides N-allylated triazoles and tetrazoles. Simultaneous control of N1/Nx-position selectivity, enantioselectivity and olefin geometry gives access to important building blocks of target-oriented synthesis. The synthetic utility is demonstrated by a gram-scale reaction and a broad substrate scope tolerating multiple functional groups. Deuterium labeling experiments and experiments with enantioenriched allenes as starting material support a plausible reaction mechanism
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Anmerkungen
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Catalysts. - 12, 10 (2022) , 1209, ISSN: 2073-4344
- Ereignis
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Veröffentlichung
- (wo)
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Freiburg
- (wer)
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Universität
- (wann)
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2022
- Urheber
- DOI
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10.3390/catal12101209
- URN
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urn:nbn:de:bsz:25-freidok-2307039
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:32 MESZ
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Beteiligte
- Sieger, Simon V.
- Lubins, Ilja
- Breit, Bernhard
- Universität
Entstanden
- 2022
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