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Literature DB >> 23249401

Asymmetric chiral ligand-directed alkene dioxygenation.

Abstract

A Pd-catalyzed asymmetric alkene 1,2-dioxygenation reaction is described. The diastereoselectivity of the reaction is controlled by tethering a chiral oxime ether directing group to the alkene substrate. The best selectivities are obtained with 8-substituted menthone-derived oxime ether auxiliaries.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2012 PMID： 23249401 PMCID： PMC3600423 DOI： 10.1021/ol303003g

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

40 in total

1. An intermolecular palladium-catalyzed diamination of unactivated alkenes.

Authors: Alvaro Iglesias; Edwin G Pérez; Kilian Muñiz
Journal: Angew Chem Int Ed Engl Date: 2010-10-25 Impact factor: 15.336

2. Construction of tetrahydrofurans by PdII/PdIV-catalyzed aminooxygenation of alkenes.

Authors: Lopa V Desai; Melanie S Sanford
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

3. Highly regioselective Pd-catalyzed intermolecular aminoacetoxylation of alkenes and evidence for cis-aminopalladation and S(N)2 C-O bond formation.

Authors: Guosheng Liu; Shannon S Stahl
Journal: J Am Chem Soc Date: 2006-06-07 Impact factor: 15.419

4. Palladium-catalyzed intermolecular aminofluorination of styrenes.

Authors: Shuifa Qiu; Tao Xu; Juan Zhou; Yinlong Guo; Guosheng Liu
Journal: J Am Chem Soc Date: 2010-03-10 Impact factor: 15.419

5. Palladium-catalyzed ring-forming aminoacetoxylation of alkenes.

Authors: Erik J Alexanian; Chulbom Lee; Erik J Sorensen
Journal: J Am Chem Soc Date: 2005-06-01 Impact factor: 15.419

Review 6. High-valent organometallic copper and palladium in catalysis.

Authors: Amanda J Hickman; Melanie S Sanford
Journal: Nature Date: 2012-04-11 Impact factor: 49.962

7. Palladium (II/IV) catalyzed cyclopropanation reactions: scope and mechanism.

Authors: Thomas W Lyons; Melanie S Sanford
Journal: Tetrahedron Date: 2009-04-18 Impact factor: 2.457

8. High-oxidation-state palladium catalysis: new reactivity for organic synthesis.

Authors: Kilian Muñiz
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

9. Mechanism of N-fluorobenzenesulfonimide promoted diamination and carboamination reactions: divergent reactivity of a Pd(IV) species.

Authors: Paul A Sibbald; Carolyn F Rosewall; Rodney D Swartz; Forrest E Michael
Journal: J Am Chem Soc Date: 2009-11-04 Impact factor: 15.419

10. Palladium-catalyzed carboamination of alkenes promoted by N-fluorobenzenesulfonimide via C-H activation of arenes.

Authors: Carolyn F Rosewall; Paul A Sibbald; Dmitry V Liskin; Forrest E Michael
Journal: J Am Chem Soc Date: 2009-07-15 Impact factor: 15.419

15 in total

Review 1. Hypervalent Iodine Reagents in High Valent Transition Metal Chemistry.

Authors: Felipe Cesar Sousa E Silva; Anthony F Tierno; Sarah E Wengryniuk
Journal: Molecules Date: 2017-05-12 Impact factor: 4.411

Review 2. Palladium(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol by a Chiral Auxiliary.

Authors: Zhen Liu; Jiahao Chen; Hou-Xiang Lu; Xiaohan Li; Yang Gao; John R Coombs; Matthew J Goldfogel; Keary M Engle
Journal: Angew Chem Int Ed Engl Date: 2019-10-08 Impact factor: 15.336

Asymmetric chiral ligand-directed alkene dioxygenation.

1. An intermolecular palladium-catalyzed diamination of unactivated alkenes.

2. Construction of tetrahydrofurans by PdII/PdIV-catalyzed aminooxygenation of alkenes.

3. Highly regioselective Pd-catalyzed intermolecular aminoacetoxylation of alkenes and evidence for cis-aminopalladation and S(N)2 C-O bond formation.

4. Palladium-catalyzed intermolecular aminofluorination of styrenes.

5. Palladium-catalyzed ring-forming aminoacetoxylation of alkenes.

Review 6. High-valent organometallic copper and palladium in catalysis.

7. Palladium (II/IV) catalyzed cyclopropanation reactions: scope and mechanism.

8. High-oxidation-state palladium catalysis: new reactivity for organic synthesis.

9. Mechanism of N-fluorobenzenesulfonimide promoted diamination and carboamination reactions: divergent reactivity of a Pd(IV) species.

10. Palladium-catalyzed carboamination of alkenes promoted by N-fluorobenzenesulfonimide via C-H activation of arenes.

Review 1. Hypervalent Iodine Reagents in High Valent Transition Metal Chemistry.

Review 2. Palladium(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol by a Chiral Auxiliary.

3. Surprisingly Facile C-H Activation in the Course of Oxime-Directed Catalytic Asymmetric Hydroboration.

4. Aerobic palladium-catalyzed dioxygenation of alkenes enabled by catalytic nitrite.

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

6. Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate.

7. Directed, Palladium(II)-Catalyzed Enantioselective anti-Carboboration of Alkenyl Carbonyl Compounds.

8. Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration.

9. Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether Directing Group for Pd(II) Catalysis.

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