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Literature DB >> 12583738

New palladium(II)-catalyzed asymmetric 1,2-dibromo synthesis.

Arab K El-Qisairi¹, Hanan A Qaseer, George Katsigras, Philip Lorenzi, Unnati Trivedi, Sylvia Tracz, Amy Hartman, Jason A Miller, Patrick M Henry.

Abstract

[reaction: see text] The oxidation of olefins by chiral monometallic and bimetallic Pd(II)-Cu(II) catalysts in bromide-containing aqueous-THF reaction mixtures produced chiral 1,2-dibromides. With alpha-olefins, the ee's were about 95% while most of the internal alkenes gave somewhat lower enantioselectivities ( approximately 80%).

Entities: Chemical

Year: 2003 PMID： 12583738 DOI： 10.1021/ol0273093

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

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Cited

11 in total

1. Lewis base catalysis of bromo- and iodolactonization, and cycloetherification.

Authors: Scott E Denmark; Matthew T Burk
Journal: Proc Natl Acad Sci U S A Date: 2010-08-12 Impact factor: 11.205

2. Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.

Authors: Matthew L Landry; Dennis X Hu; Grace M McKenna; Noah Z Burns
Journal: J Am Chem Soc Date: 2016-04-08 Impact factor: 15.419

Review 3. Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.

Authors: Richard I McDonald; Guosheng Liu; Shannon S Stahl
Journal: Chem Rev Date: 2011-03-23 Impact factor: 60.622

New palladium(II)-catalyzed asymmetric 1,2-dibromo synthesis.

1. Lewis base catalysis of bromo- and iodolactonization, and cycloetherification.

2. Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.

Review 3. Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.

Review 4. Catalytic Enantioselective Dihalogenation in Total Synthesis.

5. Formal Asymmetric Hydrobromination of Styrenes via Copper-Catalyzed 1,3-Halogen Migration.

6. Palladium-catalyzed oxidative arylhalogenation of alkenes: synthetic scope and mechanistic insights.

Review 7. Catalytic, Stereoselective Dihalogenation of Alkenes: Challenges and Opportunities.

Review 8. Catalytic Enantioselective Functionalization of Unactivated Terminal Alkenes.

Review 9. Stereoselective Halogenation in Natural Product Synthesis.

10. Reinvestigation of a Catalytic, Enantioselective Alkene Dibromination and Chlorohydroxylation.