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Literature DB >> 23312005

C2-symmetric cyclic selenium-catalyzed enantioselective bromoaminocyclization.

Feng Chen¹, Chong Kiat Tan, Ying-Yeung Yeung.

Abstract

A catalytic asymmetric bromocyclization of trisubstituted olefinic amides that uses a C(2)-symmetric mannitol-derived cyclic selenium catalyst and a stoichiometric amount of N-bromophthalimide is reported. The resulting enantioenriched pyrrolidine products, which contain two stereogenic centers, can undergo rearrangement to yield 2,3-disubstituted piperidines with excellent diastereoselectivity and enantiospecificity.

Entities: Chemical

Mesh：

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Year: 2013 PMID： 23312005 DOI： 10.1021/ja311202e

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

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Cited

15 in total

1. Catalytic, Enantioselective Synthesis of Cyclic Carbamates from Dialkyl Amines by CO₂-Capture: Discovery, Development, and Mechanism.

Authors: Roozbeh Yousefi; Thomas J Struble; Jenna L Payne; Mahesh Vishe; Nathan D Schley; Jeffrey N Johnston
Journal: J Am Chem Soc Date: 2018-12-24 Impact factor: 15.419

2. Development and mechanism of an enantioselective bromocycloetherification reaction via Lewis base/chiral Brønsted acid cooperative catalysis.

Authors: Scott E Denmark; Matthew T Burk
Journal: Chirality Date: 2013-11-07 Impact factor: 2.437

3. Catalytic Aminohalogenation of Alkenes and Alkynes.

Authors: Sherry R Chemler; Michael T Bovino
Journal: ACS Catal Date: 2013-06-07 Impact factor: 13.084

4. Regio- and Diastereoselective Synthesis of Highly Substituted, Oxygenated Piperidines from Tetrahydropyridines.

Authors: Shuming Chen; Brandon Q Mercado; Robert G Bergman; Jonathan A Ellman
Journal: J Org Chem Date: 2015-06-22 Impact factor: 4.354

5. Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications.

Authors: Daniel W Klosowski; J Caleb Hethcox; Daniel H Paull; Chao Fang; James R Donald; Christopher R Shugrue; Andrew D Pansick; Stephen F Martin
Journal: J Org Chem Date: 2018-05-22 Impact factor: 4.354

6. Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.

Authors: Rong Zhu; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2015-06-23 Impact factor: 15.419

C2-symmetric cyclic selenium-catalyzed enantioselective bromoaminocyclization.

1. Catalytic, Enantioselective Synthesis of Cyclic Carbamates from Dialkyl Amines by CO₂-Capture: Discovery, Development, and Mechanism.

2. Development and mechanism of an enantioselective bromocycloetherification reaction via Lewis base/chiral Brønsted acid cooperative catalysis.

3. Catalytic Aminohalogenation of Alkenes and Alkynes.

4. Regio- and Diastereoselective Synthesis of Highly Substituted, Oxygenated Piperidines from Tetrahydropyridines.

5. Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications.

6. Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.

7. Solid-State ⁷⁷Se NMR of Organoselenium Compounds through Cross Polarization Magic Angle Spinning (CPMAS) Method.

8. Oxoammonium salts are catalysing efficient and selective halogenation of olefins, alkynes and aromatics.

9. Iron(II)-catalyzed asymmetric intramolecular olefin aminochlorination using chloride ion.

10. Absolute and relative facial selectivities in organocatalytic asymmetric chlorocyclization reactions.