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Literature DB >> 19711900

Catalytic enantioselective intramolecular redox reactions: ring-fused tetrahydroquinolines.

Sandip Murarka¹, Indubhusan Deb, Chen Zhang, Daniel Seidel.

Abstract

The first example of a catalytic enantioselective intramolecular hydride shift/ring closure reaction is reported. This redox neutral reaction cascade allows for the efficient formation of ring-fused tetrahydroquinolines in high enantioselectivities.

Entities: Chemical

Year: 2009 PMID： 19711900 DOI： 10.1021/ja905213f

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

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Cited

22 in total

1. Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors: Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal: Chem Rev Date: 2021-05-21 Impact factor: 60.622

2. Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation.

Authors: Li Cui; Longwu Ye; Liming Zhang
Journal: Chem Commun (Camb) Date: 2010-03-30 Impact factor: 6.222

3. Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

Authors: Matthew T Richers; Indubhusan Deb; Alena Yu Platonova; Chen Zhang; Daniel Seidel
Journal: Synthesis (Stuttg) Date: 2013-10-06 Impact factor: 3.157

10. C-H Functionalization of Amines via Alkene-Derived Nucleophiles through Cooperative Action of Chiral and Achiral Lewis Acid Catalysts: Applications in Enantioselective Synthesis.

Authors: Ming Shang; Jessica Z Chan; Min Cao; Yejin Chang; Qifan Wang; Brennan Cook; Sebastian Torker; Masayuki Wasa
Journal: J Am Chem Soc Date: 2018-08-10 Impact factor: 15.419

Catalytic enantioselective intramolecular redox reactions: ring-fused tetrahydroquinolines.

1. Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

2. Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation.

3. Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

4. Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

5. Rh2(II)-catalyzed intramolecular aliphatic C-H bond amination reactions using aryl azides as the N-atom source.

6. Redox-neutral α-arylation of amines.

7. Redox-neutral copper(II) carboxylate catalyzed α-alkynylation of amines.

8. Intramolecular Redox-Mannich Reactions: Facile Access to the Tetrahydroprotoberberine Core.

9. Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides.

10. C-H Functionalization of Amines via Alkene-Derived Nucleophiles through Cooperative Action of Chiral and Achiral Lewis Acid Catalysts: Applications in Enantioselective Synthesis.