Asymmetric synthesis of N-allylic indoles via regio- and enantioselective allylation of aryl hydrazines
Abstract: The asymmetric synthesis of N-allylic indoles is important for natural product synthesis and pharmaceutical research. The regio- and enantioselective N-allylation of indoles is a true challenge due to the favourable C3-allylation. We develop here a new strategy to the asymmetric synthesis of N-allylic indoles via rhodium-catalysed N-selective coupling of aryl hydrazines with allenes followed by Fischer indolization. The exclusive N-selectivities and good to excellent enantioselectivities are achieved applying a rhodium(I)/DTBM-Segphos or rhodium(I)/DTBM-Binap catalyst. This method permits the practical synthesis of valuable chiral N-allylated indoles, and avoids the N- or C-selectivity issue
- 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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Nature communications. 6 (2015), article no. 7616, DOI 10.1038/ncomms8616, issn: 2041-1723
- Schlagwort
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Naturstoff
Alkylierung
Alkaloide
Allenderivate
Alkohol
Chemische Reaktion
- Ereignis
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Veröffentlichung
- (wo)
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Freiburg
- (wer)
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Universität
- (wann)
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2018
- Urheber
- Beteiligte Personen und Organisationen
- DOI
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10.1038/ncomms8616
- URN
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urn:nbn:de:bsz:25-freidok-147214
- Rechteinformation
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Kein Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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25.03.2025, 13:52 MEZ
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- 2018
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