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Literature DB >> 16092874

Enantioselective Brønsted acid catalyzed transfer hydrogenation: organocatalytic reduction of imines.

Magnus Rueping¹, Erli Sugiono, Cengiz Azap, Thomas Theissmann, Michael Bolte.

Abstract

The first enantioselective Brønsted acid catalyzed reduction of imines has been developed. This new organocatalytic transfer hydrogenation of ketimines with Hantzsch dihydropyridine as the hydrogen source offers a mild method to various chiral amines with high enantioselectivity. The stereochemistry of the chiral amines can be rationalized by a stereochemical model derived from an X-ray crystal structure of a chiral BINOL phosphate catalyst. [reaction: see text]

Entities: Chemical

Year: 2005 PMID： 16092874 DOI： 10.1021/ol0515964

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

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Cited

25 in total

Review 1. Organocatalytic cascade reactions as a new tool in total synthesis.

Authors: Christoph Grondal; Matthieu Jeanty; Dieter Enders
Journal: Nat Chem Date: 2010-02-19 Impact factor: 24.427

Review 2. Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors: Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal: Chem Rev Date: 2011-06-28 Impact factor: 60.622

3. Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants.

Authors: Vincent Escande; Brice-Loïc Renard; Claude Grison
Journal: Environ Sci Pollut Res Int Date: 2014-09-30 Impact factor: 4.223

Enantioselective Brønsted acid catalyzed transfer hydrogenation: organocatalytic reduction of imines.

Review 1. Organocatalytic cascade reactions as a new tool in total synthesis.

Review 2. Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

3. Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants.

4. Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones.

Review 5. Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

6. Highly enantioselective hydrogenation of enamides catalyzed by chiral phosphoric acids.

7. Continuous-flow catalytic asymmetric hydrogenations: Reaction optimization using FTIR inline analysis.

8. NMR Spectroscopic Characterization of Charge Assisted Strong Hydrogen Bonds in Brønsted Acid Catalysis.

9. Reactions of biologically inspired hydride sources with B(C₆F₅)₃.

10. Brønsted Acid Catalysis-Structural Preferences and Mobility in Imine/Phosphoric Acid Complexes.