Literature DB >> 18772399

Merging photoredox catalysis with organocatalysis: the direct asymmetric alkylation of aldehydes.

David A Nicewicz1, David W C MacMillan.   

Abstract

Photoredox catalysis and organocatalysis represent two powerful fields of molecule activation that have found widespread application in the areas of inorganic and organic chemistry, respectively. We merged these two catalysis fields to solve problems in asymmetric chemical synthesis. Specifically, the enantioselective intermolecular alpha-alkylation of aldehydes has been accomplished using an interwoven activation pathway that combines both the photoredox catalyst Ru(bpy)3Cl2 (where bpy is 2,2'-bipyridine) and an imidazolidinone organocatalyst. This broadly applicable, yet previously elusive, alkylation reaction is now highly enantioselective and operationally trivial.

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Year:  2008        PMID: 18772399      PMCID: PMC2723798          DOI: 10.1126/science.1161976

Source DB:  PubMed          Journal:  Science        ISSN: 0036-8075            Impact factor:   47.728


  7 in total

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Journal:  J Am Chem Soc       Date:  2007-12-21       Impact factor: 15.419

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Authors:  Mukund P Sibi; Masayuki Hasegawa
Journal:  J Am Chem Soc       Date:  2007-03-16       Impact factor: 15.419

3.  Catalytic asymmetric Hiyama cross-couplings of racemic alpha-bromo esters.

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4.  Enantioselective organocatalytic singly occupied molecular orbital activation: the enantioselective alpha-enolation of aldehydes.

Authors:  Hye-Young Jang; Jun-Bae Hong; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2007-05-12       Impact factor: 15.419

Review 5.  Electron transfer in proteins.

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6.  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

7.  Enantioselective organocatalysis using SOMO activation.

Authors:  Teresa D Beeson; Anthony Mastracchio; Jun-Bae Hong; Kate Ashton; David W C Macmillan
Journal:  Science       Date:  2007-03-29       Impact factor: 47.728

  7 in total
  198 in total

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Authors:  Jenna L Jeffrey; Jack A Terrett; David W C MacMillan
Journal:  Science       Date:  2015-08-27       Impact factor: 47.728

4.  Oxazolines as Dual-Function Traceless Chromophores and Chiral Auxiliaries: Enantioselective Photoassisted Synthesis of Polyheterocyclic Ketones.

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5.  Enantioselective conjugate additions of α-amino radicals via cooperative photoredox and Lewis acid catalysis.

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6.  Transition metal photoredox catalysis of radical thiol-ene reactions.

Authors:  Elizabeth L Tyson; Michael S Ament; Tehshik P Yoon
Journal:  J Org Chem       Date:  2012-11-12       Impact factor: 4.354

7.  The Development of Visible-Light Photoredox Catalysis in Flow.

Authors:  Zachary J Garlets; John D Nguyen; Corey R J Stephenson
Journal:  Isr J Chem       Date:  2014-04-01       Impact factor: 3.333

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

Authors:  Peter D Morse; Tien M Nguyen; Cole L Cruz; David A Nicewicz
Journal:  Tetrahedron       Date:  2018-03-26       Impact factor: 2.457

9.  Photoredox activation for the direct β-arylation of ketones and aldehydes.

Authors:  Michael T Pirnot; Danica A Rankic; David B C Martin; David W C MacMillan
Journal:  Science       Date:  2013-03-29       Impact factor: 47.728

10.  Brønsted acid cocatalysts in photocatalytic radical addition of α-amino C-H bonds across Michael acceptors.

Authors:  Laura Ruiz Espelt; Eric M Wiensch; Tehshik P Yoon
Journal:  J Org Chem       Date:  2013-04-10       Impact factor: 4.354

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