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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

Published inOrganic Letters, vol. 21, no. 3, p. 687-691
Publication date2019
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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Citation (ISO format)
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
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ISSN of the journal1523-7060
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Creation02/01/2019 11:08:00 AM
First validation02/01/2019 11:08:00 AM
Update time03/15/2023 3:39:39 PM
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