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Literature DB >> 21466211

Selective activation of enantiotopic C(sp3)-hydrogen by means of chiral phosphoric acid: asymmetric synthesis of tetrahydroquinoline derivatives.

Keiji Mori¹, Kensuke Ehara, Kazuki Kurihara, Takahiko Akiyama.

Abstract

Chiral phosphoric acid-catalyzed asymmetric C-H functionalization has been achieved. In this process, enantiotopic C(sp(3))-hydrogen is selectively activated by chiral phosphoric acid to afford tetrahydroquinoline derivatives with excellent enantioselectivities (up to 97% ee).

Entities: Chemical

Year: 2011 PMID： 21466211 DOI： 10.1021/ja2014955

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

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Cited

25 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. 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

3. 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

4. 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

5. Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.

Authors: Longle Ma; Anirudra Paul; Martin Breugst; Daniel Seidel
Journal: Chemistry Date: 2016-11-09 Impact factor: 5.236

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

Selective activation of enantiotopic C(sp3)-hydrogen by means of chiral phosphoric acid: asymmetric synthesis of tetrahydroquinoline derivatives.

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

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

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

4. 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.

5. Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.

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. 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.