Department of Chemistry, Indian Institute of Technology Indore, Simrol, 453552, India.
Org Biomol Chem. 2021 Sep 7;19(33):7129-7133. doi: 10.1039/d1ob01322j. Epub 2021 Aug 9.
Interesting desymmetric [3 + 2] annulation reactions between p-quinamines as prochiral N-donors and 2-aroyl-1-chlorocyclopropanecarboxylates facilitated by a base are reported. This successive double Michael reaction delivered a unique class of cyclopropane-fused hydoindol-5-one frameworks, each having four contiguous stereogenic centers, with three of them being fully substituted. Moreover, this method was found to provide acceptable chemical yields with promising diastereoselectivities (dr of up to ≤95 : 5) and to work with a variety of substrates. Importantly, a polycyclic tacrine analogue used to treat Alzheimer's disease was synthesized using our developed method.
报道了在碱的促进下，p-喹啉胺作为手性 N-供体和亲电试剂 2-芳基-1-氯环丙羧酸酯之间的有趣的不对称[3+2]环加成反应。这种连续的双重迈克尔加成反应提供了一类独特的环丙烷稠合的氢吲哚-5-酮骨架，每个骨架具有四个连续的立体中心，其中三个完全取代。此外，该方法被发现具有可以接受的化学产率和良好的非对映选择性（高达≤95:5 的 dr），并且可以与多种底物一起使用。重要的是，我们开发的方法用于合成用于治疗阿尔茨海默病的多环他克林类似物。
