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Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light

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journal contribution
posted on 05.08.2020, 11:35 by Andrea Serafino, Davide Balestri, Luciano Marchiò, Max Malacria, Etienne Derat, Giovanni Maestri
Enallenes can be readily converted into two families of 3.2.0 (hetero)­bicycles with high diastereoselectivities through the combination of visible light with a suitable Ir­(III) complex (1 mol %). Two complementary pathways, namely, a photocycloaddition versus a radical chain, can then take place. Both manifolds grant complete regiocontrol of the allene difunctionalization. This is accompanied by an original 1,3-group shift using sulfonyl allenamides that deliver a congested tetrasubstituted headbridging carbon in the corresponding product.