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Photocatalyzed Intramolecular [2+2] Cycloaddition of N‐alkyl‐N‐(2‐(1‐arylvinyl)aryl)cinnamamides

By Márcio Weber Paixão, Wanderson de Souza, Bianca Matsuo, Priscilla Matos, José Tiago M. Correia Correia, Marilia S. Santos and Burkhard König

Abstract

N ‐Alkyl‐ N ‐(2‐(1‐arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular [2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta[ c ]quinolin‐3(1 H )‐ones, in yields ranging between 27‐99%, and with excellent regio‐ and diastereoselectivity. Moreover, it was also demonstrated that the intramolecular [2+2]‐cycloaddition of 1,7‐enynes ‐ after fragmentation of the cyclobutane ring ‐ leads to enyne‐metathesis‐like products

Topics: 540 Chemie, ddc:540
Publisher: 'Wiley'
Year: 2020
DOI identifier: 10.1002/chem.202003641
OAI identifier: oai:epub.uni-regensburg.de:43820
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