Asymmetric Synthesis of Pyrroloindolones by N‐Heterocyclic Carbene Catalyzed [2+3] Annulation of α‐Chloroaldehydes with Nitrovinylindoles1. Issue 51 (4th November 2013)

• Record Type: Journal Article
• Authors: Ni, Qijian; Zhang, Huan; Grossmann, André; Loh, Charles C. J.; Merkens, Carina; Enders, Dieter
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 51(2013)
• Page Start: 13562
• Page End: 13566
• Publication Date: 2013-11-04
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201305957
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>NHC‐enolate plus 3</bold>: N‐heterocyclic carbenes (NHCs) serve as organocatalysts for the [2+3] annulation of nitrovinylindoles with α‐chloroaldehydes via an intermediate azolium enolate. The method provides <italic>trans</italic>‐disubstituted pyrroloindolones with good yields and excellent diastereo‐ and enantioselectivities. Further transformations lead to tetracyclic pyrrolo[1, 2<italic>‐a</italic>]indoles with potential psychotropic and other bioactivities.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg4t3jdt1n" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>