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Literature DB >> 19067554

Lewis acid catalyzed formation of tetrahydroquinolines via an intramolecular redox process.

Sandip Murarka¹, Chen Zhang, Marlena D Konieczynska, Daniel Seidel.

Abstract

Polycyclic tetrahydroquinolines were prepared by an efficient Lewis acid catalyzed 1,5-hydride shift, ring closure sequence. Gadolinium triflate was identified as a catalyst that is superior to scandium triflate as well as other Lewis acids. An approach toward a catalytic enantioselective variant is also described.

Entities: Chemical

Mesh：

Substances：

Year: 2009 PMID： 19067554 DOI： 10.1021/ol802519r

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

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Cited

21 in total

1. 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

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

Authors: Deepankar Das; Daniel Seidel
Journal: Org Lett Date: 2013-08-19 Impact factor: 6.005

3. C-H bond functionalization via hydride transfer: formation of α-arylated piperidines and 1,2,3,4-tetrahydroisoquinolines via stereoselective intramolecular amination of benzylic C-H bonds.

Authors: Paul A Vadola; Ignacio Carrera; Dalibor Sames
Journal: J Org Chem Date: 2012-06-06 Impact factor: 4.354

10. Metal-free α-amination of secondary amines: computational and experimental evidence for azaquinone methide and azomethine ylide intermediates.

Authors: Arne Dieckmann; Matthew T Richers; Alena Yu Platonova; Chen Zhang; Daniel Seidel; K N Houk
Journal: J Org Chem Date: 2013-04-02 Impact factor: 4.354

Lewis acid catalyzed formation of tetrahydroquinolines via an intramolecular redox process.

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

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

3. C-H bond functionalization via hydride transfer: formation of α-arylated piperidines and 1,2,3,4-tetrahydroisoquinolines via stereoselective intramolecular amination of benzylic C-H bonds.

4. Redox-neutral α-arylation of amines.

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

6. Formation of N-alkylpyrroles via intermolecular redox amination.

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

8. C-H bond functionalization via hydride transfer: synthesis of dihydrobenzopyrans from ortho-vinylaryl akyl ethers.

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

10. Metal-free α-amination of secondary amines: computational and experimental evidence for azaquinone methide and azomethine ylide intermediates.