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 ...
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.
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