Oxacycle Synthesis via Intramolecular Reaction of Carbanions and Peroxides
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Summary
The intramolecular reaction of dialkyl peroxides with carbanions, generated via chemoselective metal-heteroatom exchange or deprotonation, provides a new approach to cyclic ethers by enabling a one-step annelation to form oxaospirocycles.
- Type
- article
- Published
- 2014-04-04
- Cited by
- 49
- References
- 32
- Access
- Open access
- OpenAlex
- https://openalex.org/W24702123
- Semantic Scholar
- https://api.semanticscholar.org/CorpusID:2020108
Keywords
Humanities, Art
References
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- A stereocontrolled approach to electrophilic epoxides
- Brønsted Acid catalyzed enantioselective semipinacol rearrangement for the synthesis of chiral spiroethers.
- THE BASE CATALYZED DECOMPOSITION OF A DIALKYL PEROXIDE
- Vinylic radicals are intermediates in the oxidation of vinylic lithium reagents to lithium enolates by dioxygen, but not by lithium tert-butyl peroxide
- Reactions of Grignard Reagents with Peroxy Compounds1,2
- Regio- and stereochemical course of the ring expansion of bridged bicyclic ketones to spirocyclic .alpha.-keto tetrahydrofurans.
- Synthesis of six-membered oxygenated heterocycles through carbon-oxygen bond-forming reactions
Cited by
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- N-protected 1,2-oxazetidines as a source of electrophilic oxygen: straightforward access to benzomorpholines and related heterocycles by using a reactive tether.
- Regiospecific synthesis of distally chlorinated ketones via C–C bond cleavage of cycloalkanols
- Catalytic nucleophilic fluorination by an imidazolium ionic liquid possessing trialkylphosphine oxide functionality
- Benzannulation of indoles to carbazoles and its applications for syntheses of carbazole alkaloids.
- Difunctionalization of Styrenes with Perfluoroalkyl and tert-Butylperoxy Radicals: Room Temperature Synthesis of (1-(tert-Butylperoxy)-2-perfluoroalkyl)-ethylbenzene.
- Synthesis of Ethers via Reaction of Carbanions and Monoperoxyacetals
- Oxetanes: Recent Advances in Synthesis, Reactivity, and Medicinal Chemistry.
- Catalytic Asymmetric Conjugate Addition of Carboxylic Acids via Oxa-Michael Reaction of Peroxy Hemiacetals followed by Kornblum DeLaMare Fragmentation.
- Organocatalytic, Enantioselective Synthesis of Cyclohexadienone Containing Hindered Spirocyclic Ethers through an Oxidative Dearomatization/Oxa-Michael Addition Sequence.
- Total Synthesis and Structure Revision of (±)-Clavilactone D Through Selective Cyclization of an α,β-Dicarbonyl Peroxide.
- Merging Photoredox with Brønsted Acid Catalysis: The Cross-Dehydrogenative C-O Coupling for sp3 C-H Bond Peroxidation.
- Structural Revision of the Hancock Alkaloid (-)-Galipeine.
- Developing Functionalized Peroxide Precursors for the Synthesis of Cyclic and Spirocyclic Ethers
- Aerobic Photooxidative Synthesis of β-Alkoxy Monohydroperoxides Using an Organo Photoredox Catalyst Controlled by a Base.
- Intramolecular radical cyclization approach to access highly substituted indolines and 2,3-dihydrobenzofurans under visible-light
- Iodide reagent controlled reaction pathway of iodoperoxidation of alkenes: a high regioselectivity synthesis of α- and β-iodoperoxidates under solvent-free conditions
- Reductive Cleavage of Organic Peroxides by Iron Salts and Thiols
- Total Synthesis of (-)-Mitrephorone A.
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