Literature DB >> 20831195

Enantioselective α-benzylation of aldehydes via photoredox organocatalysis.

Hui-Wen Shih1, Mark N Vander Wal, Rebecca L Grange, David W C MacMillan.   

Abstract

The first enantioselective aldehyde α-benzylation using electron-deficient aryl and heteroaryl substrates has been accomplished. The productive merger of a chiral imidazolidinone organocatalyst and a commercially available iridium photoredox catalyst in the presence of household fluorescent light directly affords the desired homobenzylic stereogenicity in good to excellent yield and enantioselectivity. The utility of this methodology has been demonstrated via rapid access to an enantioenriched drug target for angiogenesis suppression.

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Year:  2010        PMID: 20831195      PMCID: PMC3056320          DOI: 10.1021/ja106593m

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


  20 in total

1.  Tin-free radical cyclization reactions initiated by visible light photoredox catalysis.

Authors:  Joseph W Tucker; John D Nguyen; Jagan M R Narayanam; Scott W Krabbe; Corey R J Stephenson
Journal:  Chem Commun (Camb)       Date:  2010-05-28       Impact factor: 6.222

2.  Electron transfer photoredox catalysis: intramolecular radical addition to indoles and pyrroles.

Authors:  Joseph W Tucker; Jagan M R Narayanam; Scott W Krabbe; Corey R J Stephenson
Journal:  Org Lett       Date:  2010-01-15       Impact factor: 6.005

3.  Enantioselective alkylation of acyclic alpha,alpha-disubstituted tributyltin enolates catalyzed by a {Cr(salen)} complex.

Authors:  Abigail G Doyle; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Visible light-mediated intermolecular C-H functionalization of electron-rich heterocycles with malonates.

Authors:  Laura Furst; Bryan S Matsuura; Jagan M R Narayanam; Joseph W Tucker; Corey R J Stephenson
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

5.  Efficient visible light photocatalysis of [2+2] enone cycloadditions.

Authors:  Michael A Ischay; Mary E Anzovino; Juana Du; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2008-09-04       Impact factor: 15.419

6.  Nonameric porphyrin assemblies--formation and intra-assembly energy transfer reactions.

Authors:  Ken Sasaki; Kenji Sugou; Koji Miyamoto; Jyun-Ichi Hirai; Shigetaka Tsubouchi; Hiroshi Miyasaka; Akira Itaya; Yasuhisa Kuroda
Journal:  Org Biomol Chem       Date:  2004-09-06       Impact factor: 3.876

7.  Proline-catalyzed asymmetric formal alpha-alkylation of aldehydes via vinylogous iminium ion intermediates generated from arylsulfonyl indoles.

Authors:  Rafik R Shaikh; Andrea Mazzanti; Marino Petrini; Giuseppe Bartoli; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

8.  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

9.  Crossed intermolecular [2+2] cycloadditions of acyclic enones via visible light photocatalysis.

Authors:  Juana Du; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

10.  Electron-transfer photoredox catalysis: development of a tin-free reductive dehalogenation reaction.

Authors:  Jagan M R Narayanam; Joseph W Tucker; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2009-07-01       Impact factor: 15.419

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  59 in total

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

Authors:  Laura Ruiz Espelt; Iain S McPherson; Eric M Wiensch; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2015-02-16       Impact factor: 15.419

2.  Total synthesis of (+)-gliocladin C enabled by visible-light photoredox catalysis.

Authors:  Laura Furst; Jagan M R Narayanam; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

3.  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

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

Authors:  Eric D Nacsa; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2018-02-22       Impact factor: 15.419

5.  Asymmetric photoredox transition-metal catalysis activated by visible light.

Authors:  Haohua Huo; Xiaodong Shen; Chuanyong Wang; Lilu Zhang; Philipp Röse; Liang-An Chen; Klaus Harms; Michael Marsch; Gerhard Hilt; Eric Meggers
Journal:  Nature       Date:  2014-11-06       Impact factor: 49.962

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.  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

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

Review 9.  Solar synthesis: prospects in visible light photocatalysis.

Authors:  Danielle M Schultz; Tehshik P Yoon
Journal:  Science       Date:  2014-02-28       Impact factor: 47.728

10.  Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of β-Amino Esters.

Authors:  Giulia Bergonzini; Corinna S Schindler; Carl-Johan Wallentin; Eric N Jacobsen; Corey R J Stephenson
Journal:  Chem Sci       Date:  2014-01       Impact factor: 9.825

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