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One-Step Synthesis of Diaza Macrocycles by Rh(II)-Catalyzed [3 + 6 + 3 + 6] Condensations of Morpholines and α-Diazo-β-ketoesters

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Published in Organic Letters. 2019, vol. 21, no. 3, p. 687-691
Abstract Selective formation of oxonium ylides from morpholines and α-diazo-β-ketoesters was achieved. This was applied to the high-concentration (0.5 M) dirhodium-catalyzed (0.1 mol %) [3 + 6 + 3 + 6] synthesis of 18-membered ring diaza macrocycles (46%–72%). Late-stage functionalization of these derivatives is demonstrated. Mechanistic evidence for a novel (undesired) diazo decomposition pathway is also reported.
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Other version: http://pubs.acs.org/doi/10.1021/acs.orglett.8b03875
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Research group Groupe Lacour
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HOMBERG, Alexandre et al. One-Step Synthesis of Diaza Macrocycles by Rh(II)-Catalyzed [3 + 6 + 3 + 6] Condensations of Morpholines and α-Diazo-β-ketoesters. In: Organic Letters, 2019, vol. 21, n° 3, p. 687-691. doi: 10.1021/acs.orglett.8b03875 https://archive-ouverte.unige.ch/unige:113756

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Deposited on : 2019-02-01

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