ArticleAngewandte Chemie (International ed. in English)2016
Type II Anion Relay Chemistry: Exploiting Bifunctional Weinreb Amide Linchpins for the One-Pot Synthesis of Differentiated 1,3-Diketones, Pyrans, and Spiroketals.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Evolution of Anion Relay Chemistry: Construction of Architecturally Complex Natural Products.Accounts of chemical research · 2020Review
- 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
- Anion Relay Chemistry: Development of an Effective Diastereoselective [3+2] Annulation Tactic Exploiting an Aldol/Brook Rearrangement/Cyclization Cascade.Angewandte Chemie (International ed. in English) · 2017Article
- Total Synthesis of (-)-Nahuoic Acid CJournal of the American Chemical Society · 2017Article
- Designed Spiroketal Protein Modulation.Angewandte Chemie (International ed. in English) · 2017Article
- Photoredox radical conjugate addition of dithiane-2-carboxylate promoted by an iridium(iii) phenyl-tetrazole complex: a formal radical methylation of Michael acceptors.Chemical science · 2017Article
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3 authors.
Funding
Abstract
The design, synthesis, and validation of new highly effective bifunctional linchpins for type II anion relay chemistry (ARC) has been achieved. The mechanistically novel negative-charge migration that comprises the Brook rearrangement is now initiated by a stabilized tetrahedral intermediate, which is generated by nucleophilic addition to a Weinreb amide, rather than by a simple oxyanion that is generated from an epoxide. As a result, the linchpin preserves the carbonyl functionality in the ARC adducts, thus permitting access to functionally complex systems in a single flask without the need for further chemical manipulations. This tactic was validated with the one-pot preparation of monoprotected 1,3-diketones as well as pyran and spiroketal scaffolds, depending on the choice of nucleophile, electrophile, and work-up conditions.
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