Racine Sophie, Hegedüs Bence, Scopelliti Rosario, Waser Jérôme
Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015, Lausanne, Switzerland.
Chemistry. 2016 Aug 16;22(34):11997-2001. doi: 10.1002/chem.201602755. Epub 2016 Jul 19.
Efficient methods for the convergent synthesis of (poly)cyclic scaffolds are urgently needed in synthetic and medicinal chemistry. Herein, we describe new annulation reactions of thioalkynes with phthalimide-substituted donor-acceptor cyclopropanes, which gave access to highly substituted cyclopentenes and polycyclic ring systems. With silyl-thioalkynes, the Lewis acid catalyzed [3+2] annulation reaction with donor-acceptor cyclopropanes took place to afford 1-thio-cyclopenten-3-amines. On the other hand, an unprecedented polycyclic compound was formed with alkyl-thioalkynes through a reaction pathway directly involving the phthalimide group. The two transformations proceeded in good yields and tolerated a large variety of functional groups.
在合成化学和药物化学中，迫切需要高效的（多）环骨架收敛合成方法。在此，我们描述了硫代炔烃与邻苯二甲酰亚胺取代的供体-受体环丙烷的新型环化反应，该反应可用于合成高度取代的环戊烯和多环体系。对于硅烷基硫代炔烃，在路易斯酸催化下与供体-受体环丙烷发生[3+2]环化反应，得到1-硫代环戊烯-3-胺。另一方面，通过直接涉及邻苯二甲酰亚胺基团的反应途径，烷基硫代炔烃形成了一种前所未有的多环化合物。这两种转化反应产率良好，并且能耐受多种官能团。
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