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Literature DB >> 20687604

Catalytic enantioselective radical cyclization via regiodivergent epoxide opening.

Andreas Gansäuer¹, Lei Shi, Matthias Otte.

Abstract

A catalytic enantio- and diastereoselective radical cyclization using a regiodivergent epoxide opening (REO) for radical generation is described. It is demonstrated for the first time that the diastereoselectivity of cyclizations of acyclic radicals can be controlled catalytically. Building blocks for important applications in stereoselective synthesis are readily accessed.

Entities: Chemical

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Year: 2010 PMID： 20687604 DOI： 10.1021/ja105023y

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

10 in total

1. Asymmetric Induction and Enantiodivergence in Catalytic Radical C-H Amination via Enantiodifferentiative H-Atom Abstraction and Stereoretentive Radical Substitution.

Authors: Kai Lang; Sebastian Torker; Lukasz Wojtas; X Peter Zhang
Journal: J Am Chem Soc Date: 2019-07-29 Impact factor: 15.419

2. Regiodivergent reactions through catalytic enantioselective silylation of chiral diols. Synthesis of sapinofuranone A.

Authors: Jason M Rodrigo; Yu Zhao; Amir H Hoveyda; Marc L Snapper
Journal: Org Lett Date: 2011-06-28 Impact factor: 6.005

Catalytic enantioselective radical cyclization via regiodivergent epoxide opening.

1. Asymmetric Induction and Enantiodivergence in Catalytic Radical C-H Amination via Enantiodifferentiative H-Atom Abstraction and Stereoretentive Radical Substitution.

2. Regiodivergent reactions through catalytic enantioselective silylation of chiral diols. Synthesis of sapinofuranone A.

3. Asymmetric hydrovinylation of 1-vinylcycloalkenes. Reagent control of regio- and stereoselectivity.

4. Nickel-catalyzed regiodivergent opening of epoxides with aryl halides: co-catalysis controls regioselectivity.

5. Catalytic Radical Process for Enantioselective Amination of C(sp³ )-H Bonds.

6. Merging Regiodivergent Catalysis with Atom-Economical Radical Arylation.

7. Catalytic Synthesis of 1H-2-Benzoxocins: Cobalt(III)-Carbene Radical Approach to 8-Membered Heterocyclic Enol Ethers.

8. Cascade radical reaction of substrates with a carbon-carbon triple bond as a radical acceptor.

9. Triazol-substituted titanocenes by strain-driven 1,3-dipolar cycloadditions.

Review 10. New advances in titanium-mediated free radical reactions.