Nicolai Stefano, Waser Jérôme
Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, 1015, Lausanne, Switzerland.
Angew Chem Int Ed Engl. 2022 Sep 5;61(36):e202209006. doi: 10.1002/anie.202209006. Epub 2022 Jul 28.
Azepanes are important seven-membered heterocycles, which are present in numerous natural and synthetic compounds. However, the development of convergent synthetic methods to access them remains challenging. Herein, we report the Lewis acid catalyzed (4+3) annulative addition of aryl and amino donor-acceptor cyclopropanes with 2-aza-1,3-dienes. Densely substituted azepane derivatives were obtained in good to excellent yields and with high diastereoselectivity. The reaction occurred under mild conditions with ytterbium triflate as the catalyst. The use of copper triflate with a trisoxazoline (Tox) ligand led to an enantioselective transformation. The obtained cycloadducts were convenient substrates for a series of further modifications, showing the synthetic utility of these compounds.
氮杂环庚烷是重要的七元杂环，存在于众多天然和合成化合物中。然而，开发用于合成它们的汇聚合成方法仍然具有挑战性。在此，我们报道了路易斯酸催化芳基和氨基供体-受体环丙烷与2-氮杂-1,3-二烯的（4+3）环化加成反应。以良好至优异的产率和高非对映选择性得到了高度取代的氮杂环庚烷衍生物。该反应在温和条件下以三氟甲磺酸镱为催化剂进行。使用三氟甲磺酸铜与三恶唑啉（Tox）配体导致了对映选择性转化。所得到的环加成产物是一系列进一步修饰的便利底物，展示了这些化合物的合成实用性。
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