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Literature DB >> 21539367

Enantioselective bromoaminocyclization using amino-thiocarbamate catalysts.

Ling Zhou¹, Jie Chen, Chong Kiat Tan, Ying-Yeung Yeung.

Abstract

A facile and efficient enantioselective bromoaminocyclization of unsaturated sulfonamides has been developed using an amino-thiocarbamate catalyst. A range of enantioenriched pyrrolidines were prepared with up to 99% yield and 99% ee. The corresponding lactams could be obtained through oxidation of the pyrrolidines.

Entities: Chemical

Year: 2011 PMID： 21539367 DOI： 10.1021/ja201627h

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

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Cited

15 in total

1. Enantioselective bromocycloetherification by Lewis base/chiral Brønsted acid cooperative catalysis.

Authors: Scott E Denmark; Matthew T Burk
Journal: Org Lett Date: 2011-12-06 Impact factor: 6.005

2. Chiral β-Iodoamines by Urea-Catalyzed Iodocyclization of Trichloroacetimidates.

Authors: Cheyenne S Brindle; Charles S Yeung; Eric N Jacobsen
Journal: Chem Sci J Date: 2013-05-01

3. 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

4. Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer.

Authors: Michael T Bovino; Sherry R Chemler
Journal: Angew Chem Int Ed Engl Date: 2012-03-05 Impact factor: 15.336

5. 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

Enantioselective bromoaminocyclization using amino-thiocarbamate catalysts.

1. Enantioselective bromocycloetherification by Lewis base/chiral Brønsted acid cooperative catalysis.

2. Chiral β-Iodoamines by Urea-Catalyzed Iodocyclization of Trichloroacetimidates.

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

4. Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer.

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

6. Catalytic Aminohalogenation of Alkenes and Alkynes.

7. Achiral counterion control of enantioselectivity in a Brønsted acid-catalyzed iodolactonization.

8. Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides.

9. Enantioselective Aza-Sakurai Cyclizations: Dual Role of Thiourea as H-Bond Donor and Lewis Base.

10. Iron-Catalyzed Diastereoselective Intramolecular Olefin Aminobromination with Bromide Ion.