ArticleAngewandte Chemie (International ed. in English)2017
Copper-Catalyzed Aminothiolation of 1,3-Dienes via a Dihydrothiazine Intermediate.
Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Unprecedented Copper/Iron-Cocatalyzed Homocoupling of Propargyl Ethers to Conjugated Benzofurans.JACS Au · 2025Article
- Copper-Catalyzed 1,4-Aminohydroxylation and Aminothiolation of 1,3-Dienes by Carbonyl-Assisted Migration.Chem catalysis · 2024Article
- Cycloadditions of Donor-Acceptor Cyclopropanes and -butanes using S=N-Containing Reagents: Access to Cyclic Sulfinamides, Sulfonamides, and Sulfinamidines.Angewandte Chemie (International ed. in English) · 2021Article
- Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio-, and Site-Selective Three-Component Reaction withACS catalysis · 2019Article
- Arylsulfonylacetamides as bifunctional reagents for alkene aminoarylation.Science (New York, N.Y.) · 2018Article
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Authors and funding
2 authors.
Funding
Abstract
Heteroatom-containing organic molecules are of particular interest to medicinal chemists and materials scientists. A strategy to reach these architectures via direct difunctionalization of abundant 1,3-dienes is especially attractive. Herein, we describe the development of a regio- and diastereoselective 1,4-aminothiolation of 1,3-dienes with a sulfur diimide reagent, a copper catalyst, and alkyl Grignard reagents. This unique protocol provides remote nitrogen and sulfur functionalities with high levels of stereocontrol. The reaction proceeds via a tandem hetero-Diels-Alder cycloaddition of N,N'-bis(benzenesulfonyl)sulfur diimide with 1,3-diene followed by copper-catalyzed Grignard substitution. Mechanistic studies support a copper catalyzed formation of an unprecedented [10-S-4] sulfurane that reductively eliminates to afford a 3,6-dihydrothiazine, which is selectively converted to 1,4-aminothiols.
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