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.
Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light / Serafino, A.; Balestri, D.; Marchiò, Luciano; Malacria, M.; Derat, E.; Maestri, G.. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 22:16(2020), pp. 6354-6359. [10.1021/acs.orglett.0c02193]
Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light
Serafino A.;Balestri D.;Marchiò Luciano;Maestri G.
2020-01-01
Abstract
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.| File | Dimensione | Formato | |
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