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Literature DB >> 30989757

Facile Preparation of Spirolactones by an Alkoxycarbonyl Radical Cyclization-Cross-Coupling Cascade.

Nicholas A Weires¹, Yuriy Slutskyy^1,2, Larry E Overman¹.

Abstract

An alkoxycarbonyl radical cyclization-cross-coupling cascade has been developed that allows functionalized γ-butyrolactones to be prepared in one step from simple tertiary alcohol-derived homoallylic oxalate precursors. The reaction succeeds with aryl and vinyl electrophiles and is compatible with heterocyclic fragments in both coupling partners. This chemistry allows for the rapid construction of spirolactones, which are of interest in drug discovery endeavors.

Entities: Chemical Disease

Keywords: cross-coupling; dual-catalysis; photoredox; radical cyclization; spirolactones

Year: 2019 PMID： 30989757 PMCID： PMC6555670 DOI： 10.1002/anie.201903353

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

28 in total

1. Letter: Preparation of an optically active prostaglandin intermediate via asymmetric induction.

Authors: E J Corey; H E Ensley
Journal: J Am Chem Soc Date: 1975-11-12 Impact factor: 15.419

Review 2. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors: Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal: Chem Rev Date: 2013-03-19 Impact factor: 60.622

Review 3. The use of spirocyclic scaffolds in drug discovery.

Authors: Yajun Zheng; Colin M Tice; Suresh B Singh
Journal: Bioorg Med Chem Lett Date: 2014-07-05 Impact factor: 2.823

4. Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

Authors: Zhiwei Zuo; Derek T Ahneman; Lingling Chu; Jack A Terrett; Abigail G Doyle; David W C MacMillan
Journal: Science Date: 2014-06-05 Impact factor: 47.728

5. Dual catalysis. Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis.

Authors: John C Tellis; David N Primer; Gary A Molander
Journal: Science Date: 2014-06-05 Impact factor: 47.728

6. The intramolecular carboxyarylation approach to podophyllotoxin.

Authors: Aaron J Reynolds; Andrew J Scott; Craig I Turner; Michael S Sherburn
Journal: J Am Chem Soc Date: 2003-10-08 Impact factor: 15.419

7. Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products.

Authors: Joshua Fischer; Aaron J Reynolds; Lisa A Sharp; Michael S Sherburn
Journal: Org Lett Date: 2004-04-29 Impact factor: 6.005

8. Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling.

Authors: Christopher C Nawrat; Christopher R Jamison; Yuriy Slutskyy; David W C MacMillan; Larry E Overman
Journal: J Am Chem Soc Date: 2015-08-31 Impact factor: 15.419

9. Nickel-catalyzed cross-coupling of photoredox-generated radicals: uncovering a general manifold for stereoconvergence in nickel-catalyzed cross-couplings.

Authors: Osvaldo Gutierrez; John C Tellis; David N Primer; Gary A Molander; Marisa C Kozlowski
Journal: J Am Chem Soc Date: 2015-04-08 Impact factor: 15.419

10. Visible-Light Actinometry and Intermittent Illumination as Convenient Tools to Study Ru(bpy)3Cl2 Mediated Photoredox Transformations.

Authors: Spencer P Pitre; Christopher D McTiernan; Wyatt Vine; Rebecca DiPucchio; Michel Grenier; Juan C Scaiano
Journal: Sci Rep Date: 2015-11-18 Impact factor: 4.379

7 in total

Facile Preparation of Spirolactones by an Alkoxycarbonyl Radical Cyclization-Cross-Coupling Cascade.

1. Letter: Preparation of an optically active prostaglandin intermediate via asymmetric induction.

Review 2. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Review 3. The use of spirocyclic scaffolds in drug discovery.

4. Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

5. Dual catalysis. Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis.

6. The intramolecular carboxyarylation approach to podophyllotoxin.

7. Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products.

8. Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling.

9. Nickel-catalyzed cross-coupling of photoredox-generated radicals: uncovering a general manifold for stereoconvergence in nickel-catalyzed cross-couplings.

10. Visible-Light Actinometry and Intermittent Illumination as Convenient Tools to Study Ru(bpy)3Cl2 Mediated Photoredox Transformations.

1. Ni-Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX₂ *.

2. Developments in Photoredox/Nickel Dual-Catalyzed 1,2-Difunctionalizations.

3. Ni-Catalyzed Regioselective 1,2-Dialkylation of Alkenes Enabled by the Formation of Two C(sp³)-C(sp³) Bonds.

4. Interrupting the Barton-McCombie Reaction: Aqueous Deoxygenative Trifluoromethylation of O-Alkyl Thiocarbonates.

5. Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction.

6. Dual Nickel/Photoredox-Catalyzed Site-Selective Cross-Coupling of 1,2-Bis-Boronic Esters Enabled by 1,2-Boron Shifts.

7. Nickel-Catalyzed Regioselective Alkenylarylation of γ,δ-Alkenyl Ketones via Carbonyl Coordination.