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Literature DB >> 26130043

Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes.

Eric R Welin¹, Alexander A Warkentin¹, Jay C Conrad¹, David W C MacMillan².

Abstract

The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α-cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the oxonitrile products to a wide array of medicinally relevant derivatives and heterocycles. This methodology has also been applied to the total synthesis of the lignan natural product (-)-bursehernin.

Entities: Chemical Gene Species

Keywords: aldehydes; alkylation; organocatalysis; photoredox catalysis; total synthesis

Mesh：

Substances：

Year: 2015 PMID： 26130043 PMCID： PMC4548807 DOI： 10.1002/anie.201503789

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

21 in total

Review 1. Asymmetric enamine catalysis.

Authors: Santanu Mukherjee; Jung Woon Yang; Sebastian Hoffmann; Benjamin List
Journal: Chem Rev Date: 2007-12 Impact factor: 60.622

2. Photochemical activity of a key donor-acceptor complex can drive stereoselective catalytic α-alkylation of aldehydes.

Authors: Elena Arceo; Igor D Jurberg; Ana Alvarez-Fernández; Paolo Melchiorre
Journal: Nat Chem Date: 2013-08-11 Impact factor: 24.427

3. The advent and development of organocatalysis.

Authors: David W C MacMillan
Journal: Nature Date: 2008-09-18 Impact factor: 49.962

4. The medicinal chemist's toolbox: an analysis of reactions used in the pursuit of drug candidates.

Authors: Stephen D Roughley; Allan M Jordan
Journal: J Med Chem Date: 2011-05-02 Impact factor: 7.446

5. Dissociative electron transfer to haloacetonitriles. An example of the dependency of in-cage ion-radical interactions upon the leaving group.

Authors: Annarita Cardinale; Abdirisak A Isse; Armando Gennaro; Marc Robert; Jean-Michel Savéant
Journal: J Am Chem Soc Date: 2002-11-13 Impact factor: 15.419

Review 6. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors: Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal: Chem Rev Date: 2013-03-19 Impact factor: 60.622

7. Enantioselective α-benzylation of aldehydes via photoredox organocatalysis.

Authors: Hui-Wen Shih; Mark N Vander Wal; Rebecca L Grange; David W C MacMillan
Journal: J Am Chem Soc Date: 2010-10-06 Impact factor: 15.419

8. Enantioselective direct α-amination of aldehydes via a photoredox mechanism: a strategy for asymmetric amine fragment coupling.

Authors: Giuseppe Cecere; Christian M König; Jennifer L Alleva; David W C MacMillan
Journal: J Am Chem Soc Date: 2013-07-26 Impact factor: 15.419

9. Catalytic asymmetric intramolecular alpha-alkylation of aldehydes.

Authors: Nicola Vignola; Benjamin List
Journal: J Am Chem Soc Date: 2004-01-21 Impact factor: 15.419

Review 10. Asymmetric ion-pairing catalysis.

Authors: Katrien Brak; Eric N Jacobsen
Journal: Angew Chem Int Ed Engl Date: 2012-11-28 Impact factor: 15.336

18 in total

Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes.

Review 1. Asymmetric enamine catalysis.

2. Photochemical activity of a key donor-acceptor complex can drive stereoselective catalytic α-alkylation of aldehydes.

3. The advent and development of organocatalysis.

4. The medicinal chemist's toolbox: an analysis of reactions used in the pursuit of drug candidates.

5. Dissociative electron transfer to haloacetonitriles. An example of the dependency of in-cage ion-radical interactions upon the leaving group.

Review 6. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

7. Enantioselective α-benzylation of aldehydes via photoredox organocatalysis.

8. Enantioselective direct α-amination of aldehydes via a photoredox mechanism: a strategy for asymmetric amine fragment coupling.

9. Catalytic asymmetric intramolecular alpha-alkylation of aldehydes.

Review 10. Asymmetric ion-pairing catalysis.

1. Spin-Center Shift-Enabled Direct Enantioselective α-Benzylation of Aldehydes with Alcohols.

2. Photoredox Cyanomethylation of Indoles: Catalyst Modification and Mechanism.

3. Copper-Catalyzed Alkylation of Nitroalkanes with α-Bromonitriles: Synthesis of β-Cyanonitroalkanes.

4. Asymmetric Photocatalysis Enabled by Chiral Organocatalysts.

5. Enantioselective counter-anions in photoredox catalysis: the asymmetric cation radical Diels-Alder reaction.

6. Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles.

Review 7. Photoredox-Catalyzed C-H Functionalization Reactions.

8. Photoredox Catalysis in Organic Chemistry.

Review 9. Dual Catalysis Strategies in Photochemical Synthesis.

10. Synthesis of 1,3-cis-disubstituted sterically encumbered imidazolidinone organocatalysts.