通过吲哚基铜-烯丙基中间体的催化不对称[3 + 2]环加成：吡咯并[1,2-]吲哚的非对映选择性和对映选择性组装。
Catalytic Asymmetric [3 + 2] Annulation via Indolyl Copper-Allenylidene Intermediates: Diastereo- and Enantioselective Assembly of Pyrrolo[1,2-]indoles.
机构信息
School of Pharmacy and Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, Jinhua 321004, China.
出版信息
Org Lett. 2020 Jun 5;22(11):4547-4552. doi: 10.1021/acs.orglett.0c01594. Epub 2020 May 26.
A catalytic asymmetric decarboxylative [3 + 2] annulation via indolyl copper-allenylidene amphiphilic intermediates has been developed. This protocol offers a straightforward method for the synthesis of biologically important pyrrolo[1,2-]indoles bearing contiguous quaternary and tertiary stereogenic centers with excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). In addition, the diversity-oriented synthesis of pyrrolo[1,2-]indoles was achieved via versatile transformations of the alkyne-containing cycloadducts.
发展了一种通过吲哚基铜-烯丙基两性中间体制备催化不对称脱羧[3+2]环加成的方法。该方法为合成具有连续季碳和三级手性中心的生物重要吡咯并[1,2-a]吲哚提供了一种直接的方法，具有优异的非对映选择性和对映选择性（高达>20:1 的 dr 和>99%的 ee）。此外，通过炔烃环加成产物的多种转化，实现了吡咯并[1,2-a]吲哚的多样性导向合成。
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