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可见光促进的丙二烯环加成反应合成 3,2,0 双环化合物

Orthogonal Syntheses of 3.2.0 Bicycles from Enallenes Promoted by Visible Light.

机构信息

Department of Chemistry, Life Sciences and Environmental Sustainability, Università di Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy.

Faculty of Science and Engineering, CNRS, Institut Parisien de Chimie Moléculaire (UMR CNRS 8232), 4 place Jussieu, Paris 75252 Cedex 05, France.

出版信息

Org Lett. 2020 Aug 21;22(16):6354-6359. doi: 10.1021/acs.orglett.0c02193. Epub 2020 Aug 5.

DOI:10.1021/acs.orglett.0c02193
PMID:32806183
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8010793/
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.

摘要

烯丙炔可以通过可见光与合适的 Ir(III) 配合物（1 mol %）的组合，很容易转化为具有高非对映选择性的两类 3.2.0（杂）双环体系。然后可以发生两种互补途径，即光环加成和自由基链。这两种途径都可以完全控制烯丙炔的双官能化反应。这伴随着使用磺酰基烯丙酰胺的原始 1,3-基团迁移，在相应的产物中提供了拥挤的四取代头桥接碳原子。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae91/8010793/b21f319f47eb/ol0c02193_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae91/8010793/083d5e6161de/ol0c02193_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae91/8010793/d1baf89049ba/ol0c02193_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae91/8010793/96a0833b4f0f/ol0c02193_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae91/8010793/dab378a5e2bd/ol0c02193_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae91/8010793/f759505b2f77/ol0c02193_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae91/8010793/b21f319f47eb/ol0c02193_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae91/8010793/083d5e6161de/ol0c02193_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae91/8010793/d1baf89049ba/ol0c02193_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae91/8010793/96a0833b4f0f/ol0c02193_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae91/8010793/dab378a5e2bd/ol0c02193_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae91/8010793/f759505b2f77/ol0c02193_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae91/8010793/b21f319f47eb/ol0c02193_0003.jpg

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