Journal
ORGANIC LETTERS
Volume 22, Issue 16, Pages 6354-6359Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02193
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Funding
- Departments of Excellence program of the Italian Ministry for Education, University and Research (MIUR, 2018-2022)
- UniPR
- UPMC
- CNRS
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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 WHO 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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