Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light

[Image: see text] 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 t...

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Autores principales: Serafino, Andrea, Balestri, Davide, Marchiò, Luciano, Malacria, Max, Derat, Etienne, Maestri, Giovanni
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8010793/
https://www.ncbi.nlm.nih.gov/pubmed/32806183
http://dx.doi.org/10.1021/acs.orglett.0c02193
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author Serafino, Andrea
Balestri, Davide
Marchiò, Luciano
Malacria, Max
Derat, Etienne
Maestri, Giovanni
author_facet Serafino, Andrea
Balestri, Davide
Marchiò, Luciano
Malacria, Max
Derat, Etienne
Maestri, Giovanni
author_sort Serafino, Andrea
collection PubMed
description [Image: see text] 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.
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spelling pubmed-80107932021-03-31 Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light Serafino, Andrea Balestri, Davide Marchiò, Luciano Malacria, Max Derat, Etienne Maestri, Giovanni Org Lett [Image: see text] 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. American Chemical Society 2020-08-05 2020-08-21 /pmc/articles/PMC8010793/ /pubmed/32806183 http://dx.doi.org/10.1021/acs.orglett.0c02193 Text en Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Serafino, Andrea
Balestri, Davide
Marchiò, Luciano
Malacria, Max
Derat, Etienne
Maestri, Giovanni
Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light
title Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light
title_full Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light
title_fullStr Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light
title_full_unstemmed Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light
title_short Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light
title_sort orthogonal syntheses of 3.2.0 bicycles from enallenes promoted by visible light
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8010793/
https://www.ncbi.nlm.nih.gov/pubmed/32806183
http://dx.doi.org/10.1021/acs.orglett.0c02193
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