Literature DB >> 22616631

Enantioselective α-vinylation of aldehydes via the synergistic combination of copper and amine catalysis.

Eduardas Skucas1, David W C MacMillan.   

Abstract

The enantioselective α-vinylation of aldehydes using vinyl iodonium triflate salts has been accomplished via the synergistic combination of copper and chiral amine catalysis. These mild catalytic conditions provide a direct route for the enantioselective construction of enolizable α-formyl vinylic stereocenters without racemization or olefin transposition. These high-value coupling adducts are readily converted into a variety of useful olefin synthons.

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Year:  2012        PMID： 22616631      PMCID： PMC3415571          DOI： 10.1021/ja303116v

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


  32 in total

1.  Cooperative catalytic reactions using organocatalysts and transition-metal catalysts: enantioselective propargylic alkylation of propargylic alcohols with aldehydes.

Authors:  Masahiro Ikeda; Yoshihiro Miyake; Yoshiaki Nishibayashi
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-24       Impact factor: 15.336

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

Authors:  Xing Dai; Neil A Strotman; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2008-02-27       Impact factor: 15.419

3.  Contemporaneous dual catalysis: chemoselective cross-coupling of catalytic vanadium-allenoate and π-allylpalladium intermediates.

Authors:  Barry M Trost; Xinjun Luan; Yan Miller
Journal:  J Am Chem Soc       Date:  2011-07-22       Impact factor: 15.419

4.  alpha-Vinylation of 1,3-Dicarbonyl Compounds with Alkenyl(aryl)iodonium Tetrafluoroborates: Effects of Substituents on the Aromatic Ring and of Radical Inhibitors.

Authors:  Masahito Ochiai; Toshifusa Shu; Takema Nagaoka; Yutaka Kitagawa
Journal:  J Org Chem       Date:  1997-04-04       Impact factor: 4.354

5.  Enantioselective alkenylation via nickel-catalyzed cross-coupling with organozirconium reagents.

Authors:  Sha Lou; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-04-14       Impact factor: 15.419

6.  Oxidative C-H activation/C-C bond forming reactions: synthetic scope and mechanistic insights.

Authors:  Dipannita Kalyani; Nicholas R Deprez; Lopa V Desai; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2005-05-25       Impact factor: 15.419

7.  Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions.

Authors:  Robert J Phipps; Neil P Grimster; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2008-06-11       Impact factor: 15.419

8.  Cooperative dual catalysis: application to the highly enantioselective conjugate cyanation of unsaturated imides.

Authors:  Glenn M Sammis; Hiroshi Danjo; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2004-08-18       Impact factor: 15.419

9.  Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand.

Authors:  Alexander M Taylor; Ryan A Altman; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

10.  Cooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to gamma-lactams.

Authors:  Dustin E A Raup; Benoit Cardinal-David; Dane Holte; Karl A Scheidt
Journal:  Nat Chem       Date:  2010-07-18       Impact factor: 24.427
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  9 in total

1.  Mechanistic Studies of Gold and Palladium Cooperative Dual-Catalytic Cross-Coupling Systems.

Authors:  Mohammad Al-Amin; Katrina E Roth; Suzanne A Blum
Journal:  ACS Catal       Date:  2014-02-07       Impact factor: 13.084

2.  Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis.

Authors:  Jason M Stevens; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-08-05       Impact factor: 15.419

3.  Mechanistic Studies of Azaphilic versus Carbophilic Activation by Gold(I) in the Gold/Palladium Dual-Catalyzed Rearrangement of Alkenyl Vinyl Aziridines.

Authors:  Joshua J Hirner; Katrina E Roth; Yili Shi; Suzanne A Blum
Journal:  Organometallics       Date:  2012-10-08       Impact factor: 3.876

4.  Simple catalytic mechanism for the direct coupling of α-carbonyls with functionalized amines: a one-step synthesis of Plavix.

Authors:  Ryan W Evans; Jason R Zbieg; Shaolin Zhu; Wei Li; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-10-16       Impact factor: 15.419

5.  Alkenylation of C(sp3 )-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts.

Authors:  Chuan Liu; Qiu Wang
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-15       Impact factor: 15.336

6.  Selectivity, Compatibility, Downstream Functionalization, and Silver Effect in the Gold and Palladium Dual-Catalytic Synthesis of Lactones.

Authors:  Mohammad Al-Amin; Joel S Johnson; Suzanne A Blum
Journal:  Organometallics       Date:  2014-09-09       Impact factor: 3.876

7.  Towards an asymmetric organocatalytic α-cyanation of β-ketoesters.

Authors:  Raghunath Chowdhury; Johannes Schörgenhumer; Johanna Novacek; Mario Waser
Journal:  Tetrahedron Lett       Date:  2015-04-01       Impact factor: 2.415

8.  Nitro-enabled catalytic enantioselective formal umpolung alkenylation of β-ketoesters.

Authors:  Abhijnan Ray Choudhury; Madhu Sudan Manna; Santanu Mukherjee
Journal:  Chem Sci       Date:  2017-08-02       Impact factor: 9.825

9.  Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions.

Authors:  Laura Castoldi; Ester Maria Di Tommaso; Marcus Reitti; Barbara Gräfen; Berit Olofsson
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-15       Impact factor: 15.336
  9 in total

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