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Literature DB >> 18044907

Copper(II) carboxylate-promoted intramolecular carboamination of alkenes for the synthesis of polycyclic lactams.

Abstract

The copper(II) carboxylate-promoted intramolecular carboamination reactions of variously substituted gamma-alkenyl amides have been investigated. These oxidative cyclization reactions efficiently provide polycyclic lactams, useful intermediates in nitrogen heterocycle synthesis, in good to excellent yields. The efficiency of the carboamination process is dependent upon the structure of the amide backbone as well as the nitrogen substituent.

Entities: Chemical

Mesh：

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Year: 2007 PMID： 18044907 PMCID： PMC2590668 DOI： 10.1021/ol702401w

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

16 in total

1. A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles.

Authors: A Klapars; J C Antilla; X Huang; S L Buchwald
Journal: J Am Chem Soc Date: 2001-08-08 Impact factor: 15.419

2. An unusual approach to spirolactones and related structures.

Authors: Soizic Guindeuil; Samir Z Zard
Journal: Chem Commun (Camb) Date: 2006-01-06 Impact factor: 6.222

3. Mild conditions for the synthesis of functionalized pyrrolidines via Pd-catalyzed carboamination reactions.

Authors: Myra Beaudoin Bertrand; Matthew L Leathen; John P Wolfe
Journal: Org Lett Date: 2007-02-01 Impact factor: 6.005

4. Direct coupling of indoles with carbonyl compounds: short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families.

Authors: Phil S Baran; Jeremy M Richter
Journal: J Am Chem Soc Date: 2004-06-23 Impact factor: 15.419

5. Synthesis of heterocycles via palladium pi-olefin and pi-alkyne chemistry.

Authors: Gilson Zeni; Richard C Larock
Journal: Chem Rev Date: 2004-05 Impact factor: 60.622

6. Palladium-catalyzed highly stereoselective synthesis of N-aryl-3-arylmethylisoxazolidines via tandem arylation of O-homoallylhydroxylamines.

Authors: Jinsong Peng; Wenqing Lin; Shixue Yuan; Yuanwei Chen
Journal: J Org Chem Date: 2007-03-17 Impact factor: 4.354

7. Copper(II) acetate promoted oxidative cyclization of arylsulfonyl-o-allylanilines.

Authors: Eric S Sherman; Sherry R Chemler; Tai Boon Tan; Oksana Gerlits
Journal: Org Lett Date: 2004-05-13 Impact factor: 6.005

8. Pd(II)-catalyzed enantioselective oxidative tandem cyclization reactions. Synthesis of indolines through C-N and C-C bond formation.

Authors: Kai-Tai Yip; Min Yang; Ka-Lun Law; Nian-Yong Zhu; Dan Yang
Journal: J Am Chem Soc Date: 2006-03-15 Impact factor: 15.419

9. Pyrrolidine and piperidine formation via copper(II) carboxylate-promoted intramolecular carboamination of unactivated olefins: diastereoselectivity and mechanism.

Authors: Eric S Sherman; Peter H Fuller; Dhanalakshmi Kasi; Sherry R Chemler
Journal: J Org Chem Date: 2007-04-12 Impact factor: 4.354

10. A new tin-free source of amidyl radicals.

Authors: Fabien Gagosz; Cecile Moutrille; Samir Z Zard
Journal: Org Lett Date: 2002-08-08 Impact factor: 6.005

14 in total

1. Use of aryl chlorides as electrophiles in Pd-catalyzed alkene difunctionalization reactions.

Authors: Brandon R Rosen; Joshua E Ney; John P Wolfe
Journal: J Org Chem Date: 2010-04-16 Impact factor: 4.354

2. Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans.

Authors: Yan Miller; Lei Miao; Azade S Hosseini; Sherry R Chemler
Journal: J Am Chem Soc Date: 2012-07-05 Impact factor: 15.419

3. Diastereo- and enantioselective copper-catalyzed intramolecular carboamination of alkenes for the synthesis of hexahydro-1H-benz[f]indoles.

Authors: Lei Miao; Imranul Haque; Maria R Manzoni; Weng Siong Tham; Sherry R Chemler
Journal: Org Lett Date: 2010-11-05 Impact factor: 6.005

4. Total synthesis of (S)-(+)-tylophorine via enantioselective intramolecular alkene carboamination.

Authors: Wei Zeng; Sherry R Chemler
Journal: J Org Chem Date: 2008-06-28 Impact factor: 4.354

5. Copper-promoted and copper-catalyzed intermolecular alkene diamination.

Authors: Fatima C Sequeira; Benjamin W Turnpenny; Sherry R Chemler
Journal: Angew Chem Int Ed Engl Date: 2010-08-23 Impact factor: 15.336

6. Evolution of copper(II) as a new alkene amination promoter and catalyst.

Authors: Sherry R Chemler
Journal: J Organomet Chem Date: 2011-01-01 Impact factor: 2.369

7. Evidence for alkene cis-aminocupration, an aminooxygenation case study: kinetics, EPR spectroscopy, and DFT calculations.

Authors: Monissa C Paderes; Lee Belding; Branden Fanovic; Travis Dudding; Jerome B Keister; Sherry R Chemler
Journal: Chemistry Date: 2012-01-11 Impact factor: 5.236

8. Pd-catalyzed carboamination of oxazolidin-2-ones: a stereoselective route to trans-2,5-disubstituted pyrrolidines.

Authors: Georgia S Lemen; John P Wolfe
Journal: Org Lett Date: 2010-05-21 Impact factor: 6.005

9. Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation.

Authors: Katrina H Jensen; Tejas P Pathak; Yang Zhang; Matthew S Sigman
Journal: J Am Chem Soc Date: 2009-12-02 Impact factor: 15.419

10. Diastereoselective pyrrolidine synthesis via copper promoted intramolecular aminooxygenation of alkenes: formal synthesis of (+)-monomorine.

Authors: Monissa C Paderes; Sherry R Chemler
Journal: Org Lett Date: 2009-05-07 Impact factor: 6.005