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Literature DB >> 19722670

Enantioselective alpha-trifluoromethylation of aldehydes via photoredox organocatalysis.

David A Nagib¹, Mark E Scott, David W C MacMillan.

Abstract

The first enantioselective, organocatalytic alpha-trifluoromethylation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.

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Year: 2009 PMID： 19722670 PMCID： PMC3310169 DOI： 10.1021/ja9053338

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

19 in total

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Journal: Org Lett Date: 2005-10-27 Impact factor: 6.005

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Authors: Jun-An Ma; Dominique Cahard
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8. 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

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
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93 in total

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Journal: J Am Chem Soc Date: 2012-05-24 Impact factor: 15.419

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Journal: J Am Chem Soc Date: 2016-02-16 Impact factor: 15.419

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Journal: J Am Chem Soc Date: 2015-02-16 Impact factor: 15.419

6. 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

7. Combining Transition Metal Catalysis with Radical Chemistry: Dramatic Acceleration of Palladium-Catalyzed C-H Arylation with Diaryliodonium Salts.

Authors: Sharon R Neufeldt; Melanie S Sanford
Journal: Adv Synth Catal Date: 2012-12-14 Impact factor: 5.837

8. The productive merger of iodonium salts and organocatalysis: a non-photolytic approach to the enantioselective alpha-trifluoromethylation of aldehydes.

Authors: Anna E Allen; David W C Macmillan
Journal: J Am Chem Soc Date: 2010-04-14 Impact factor: 15.419

9. 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

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