ArticleAngewandte Chemie (International ed. in English)2014
Through-bond/through-space anion relay chemistry exploiting vinylepoxides as bifunctional linchpins.
Article in Angewandte Chemie (International ed. in English), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Evolution of Anion Relay Chemistry: Construction of Architecturally Complex Natural Products.Accounts of chemical research · 2020Review
- Reactions of 2-Aryl-1,3-Dithianes and [1.1.1]Propellane.Angewandte Chemie (International ed. in English) · 2019Article
- Dithiane-directed Rh(iii)-catalyzed amidation of unactivated C(spChemical science · 2019Article
- Synthetic Access to the Mandelalide Family of Macrolides: Development of an Anion Relay Chemistry Strategy.The Journal of organic chemistry · 2018Article
- Pot-Economy Autooxidative Condensation of 2-Aryl-2-lithio-1,3-dithianes.The Journal of organic chemistry · 2018Article
- Total Synthesis of (-)-Nahuoic Acid CJournal of the American Chemical Society · 2017Article
- Organic synthesis in the Smith Group: a personal selection of a dozen lessons learned at the University of Pennsylvania.The Journal of antibiotics · 2016Article
- Reversed-Polarity Synthesis of Diaryl Ketones through Palladium-Catalyzed Direct Arylation of 2-Aryl-1,3-dithianes.Advanced synthesis & catalysis · 2014Article
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Authors and funding
3 authors.
Funding
Abstract
The development of new bifunctional linchpins that permit the union of diverse building blocks is essential for the synthetic utility of anion relay chemistry (ARC). The design, synthesis, and validation of three vinylepoxide linchpins for through-bond/through-space ARC are now reported. For negative charge migration, this class of bifunctional linchpins employs initial through-bond ARC by an SN 2' reaction, followed by through-space ARC exploiting a 1,4-Brook rearrangement. The trans-disubstituted vinylepoxide linchpin yields a mixture of E/Z isomers, whereas the cis-disubstituted and the trans-trisubstituted vinylepoxide linchpins proceed to deliver three-component adducts with excellent E selectivity.
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