Literature DB >> 23889497

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

Jason M Stevens1, David W C MacMillan.   

Abstract

The enantioselective α-alkenylation of aldehydes has been accomplished using boronic acids via the synergistic combination of copper and chiral amine catalysis. The merger of two highly utilized and robust catalytic systems has allowed for the development of a mild and operationally trivial protocol for the direct formation of α-formyl olefins employing common building blocks for organic synthesis.

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Year:  2013        PMID: 23889497      PMCID: PMC3785792          DOI: 10.1021/ja406356c

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


  30 in total

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Authors:  Madeleine E Kieffer; Kangway V Chuang; Sarah E Reisman
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3.  Enantioselective copper-catalyzed construction of aryl pyrroloindolines via an arylation-cyclization cascade.

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4.  Enantioselective α-arylation of N-acyloxazolidinones with copper(II)-bisoxazoline catalysts and diaryliodonium salts.

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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.  Copper-catalyzed arylative Meyer-Schuster rearrangement of propargylic alcohols to complex enones using diaryliodonium salts.

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7.  Total diastereofacial selective iodofunctionalization of terpene derivatives based on Ipy2BF4.

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8.  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

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.  Boroxine chemistry and applications: A perspective.

Authors:  Andrew L Korich; Peter M Iovine
Journal:  Dalton Trans       Date:  2009-11-05       Impact factor: 4.390

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  6 in total

1.  Palladium-catalyzed enantioselective Heck alkenylation of acyclic alkenols using a redox-relay strategy.

Authors:  Harshkumar H Patel; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-03-09       Impact factor: 15.419

2.  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

3.  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

4.  Ligand-controlled asymmetric arylation of aliphatic α-amino anion equivalents.

Authors:  Ye Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2014-03-13       Impact factor: 15.419

5.  Radical asymmetric intramolecular α-cyclopropanation of aldehydes towards bicyclo[3.1.0]hexanes containing vicinal all-carbon quaternary stereocenters.

Authors:  Liu Ye; Qiang-Shuai Gu; Yu Tian; Xiang Meng; Guo-Cong Chen; Xin-Yuan Liu
Journal:  Nat Commun       Date:  2018-01-15       Impact factor: 14.919

6.  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

  6 in total

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