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Photocatalyzed Intramolecular [2+2] Cycloaddition of N ‐Alkyl‐ N‐( 2‐(1‐arylvinyl)aryl)cinnamamides
Author(s) -
Souza Wanderson C.,
Matsuo Bianca T.,
Matos Priscilla M.,
Correia José Tiago M.,
Santos Marilia S.,
König Burkhard,
Paixão Marcio W.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202003641
Subject(s) - intramolecular force , cyclobutane , cycloaddition , chemistry , aryl , oxetane , alkyl , enyne , stereochemistry , ring (chemistry) , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
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 20–99 %, and with excellent regio‐ and diastereoselectivity. Moreover, it was demonstrated that the intramolecular [2+2]‐cycloaddition of 1,7‐enynes—after fragmentation of the cyclobutane ring—leads to enyne‐metathesis‐like products.