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Literature DB >> 20701277

Enantioselective organocatalytic C-H bond functionalization via tandem 1,5-hydride transfer/ring closure: asymmetric synthesis of tetrahydroquinolines.

Young Ku Kang¹, Sun Mi Kim, Dae Young Kim.

Abstract

The first organocatalytic enantioselective intramolecular 1,5-hydride transfer/ring closure reaction is described. This redox neutral reaction cascade allows for the efficient formation of ring-fused tetrahydroquinolines in high enantioselectivities.

Entities: Chemical

Mesh：

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Year: 2010 PMID： 20701277 DOI： 10.1021/ja103786c

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

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Cited

30 in total

1. A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones.

Authors: Dillon H Miles; Joan Guasch; F Dean Toste
Journal: J Am Chem Soc Date: 2015-06-12 Impact factor: 15.419

2. Computationally guided stereocontrol of the combined C-H functionalization/Cope rearrangement.

Authors: Yajing Lian; Kenneth I Hardcastle; Huw M L Davies
Journal: Angew Chem Int Ed Engl Date: 2011-08-30 Impact factor: 15.336

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

4. Cascade intramolecular N-arylation/intermolecular carboamination reactions for the construction of tricyclic heterocycles.

Authors: Georgia S Lemen; John P Wolfe
Journal: Org Lett Date: 2011-05-23 Impact factor: 6.005

Enantioselective organocatalytic C-H bond functionalization via tandem 1,5-hydride transfer/ring closure: asymmetric synthesis of tetrahydroquinolines.

1. A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones.

2. Computationally guided stereocontrol of the combined C-H functionalization/Cope rearrangement.

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. Cascade intramolecular N-arylation/intermolecular carboamination reactions for the construction of tricyclic heterocycles.

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

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. A one-pot multicomponent strategy for stereospecific construction of tricyclic pyrrolo[1,2-a]quinolines.

10. Redox-neutral α,β-difunctionalization of cyclic amines.