Literature DB >> 21678927

Effect of counterion structure on rates and diastereoselectivities in α,β-unsaturated iminium-ion Diels-Alder reactions.

David Marcoux1, Pascal Bindschädler, Alexander W H Speed, Anna Chiu, Joseph E Pero, George A Borg, David A Evans.   

Abstract

The use of cyclic α,β-unsaturated iminium-ion dienophiles is documented in two highly diastereoselective Diels-Alder (DA) reactions. The dienophilic counterion was found to have a significant effect on reactivity.
© 2011 American Chemical Society

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Year:  2011        PMID： 21678927      PMCID： PMC3408793          DOI： 10.1021/ol201448h

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  17 in total

1.  Characterization of spirolides a, c, and 13-desmethyl c, new marine toxins isolated from toxic plankton and contaminated shellfish.

Authors:  T Hu; I W Burton; A D Cembella; J M Curtis; M A Quilliam; J A Walter; J L Wright
Journal:  J Nat Prod       Date:  2001-03       Impact factor: 4.050

2.  Diels-Alder reactions of cyclic isoimidium salts.

Authors:  Robert K Boeckman; Yan Miller; Todd R Ryder
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

3.  A formal total synthesis of (+)-pinnatoxin A.

Authors:  Satoshi Sakamoto; Hayato Sakazaki; Koji Hagiwara; Kei Kamada; Kento Ishii; Takeshi Noda; Masayuki Inoue; Masahiro Hirama
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-03       Impact factor: 15.336

4.  Enantioselective total synthesis of the osteoclastogenesis inhibitor (+)-symbioimine.

Authors:  Justin Kim; Regan J Thomson
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  The advent and development of organocatalysis.

Authors:  David W C MacMillan
Journal:  Nature       Date:  2008-09-18       Impact factor: 49.962

6.  Counterion effects in iminium-activated electrophilic aromatic substitutions of pyrroles.

Authors:  Sami Lakhdar; Herbert Mayr
Journal:  Chem Commun (Camb)       Date:  2010-12-07       Impact factor: 6.222

7.  Marine Toxins with Spiroimine Rings: Total Synthesis of Pinnatoxin A.

Authors:  Stéphane Beaumont; Elizabeth A Ilardi; Nicholas D C Tappin; Armen Zakarian
Journal:  European J Org Chem       Date:  2010-10-01

8.  Total synthesis of (+/-)-symbioimine.

Authors:  Yefen Zou; Qinglin Che; Barry B Snider
Journal:  Org Lett       Date:  2006-11-23       Impact factor: 6.005

9.  The first general enantioselective catalytic Diels-Alder reaction with simple alpha,beta-unsaturated ketones.

Authors:  Alan B Northrup; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

10.  Total synthesis of (+)-pinnatoxin A.

Authors:  Craig E Stivala; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2008-03-01       Impact factor: 15.419
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  4 in total

1.  Total Synthesis of the Galbulimima Alkaloids Himandravine and GB17 Using Biomimetic Diels-Alder Reactions of Double Diene Precursors.

Authors:  Reed T Larson; Ryan P Pemberton; Jenna M Franke; Dean J Tantillo; Regan J Thomson
Journal:  J Am Chem Soc       Date:  2015-08-25       Impact factor: 15.419

2.  Stability of cyclic imine toxins: interconversion of pinnatoxin amino ketone and pinnatoxin A in aqueous media.

Authors:  Jeffrey J Jackson; Craig E Stivala; Bogdan I Iorga; Jordi Molgó; Armen Zakarian
Journal:  J Org Chem       Date:  2012-11-06       Impact factor: 4.354

3.  A quantitative approach to nucleophilic organocatalysis.

Authors:  Herbert Mayr; Sami Lakhdar; Biplab Maji; Armin R Ofial
Journal:  Beilstein J Org Chem       Date:  2012-09-05       Impact factor: 2.883

4.  Total Synthesis, Stereochemical Assignment, and Divergent Enantioselective Enzymatic Recognition of Larreatricin.

Authors:  Harry J Martin; Ioannis Kampatsikas; Rik Oost; Matthias Pretzler; Emir Al-Sayed; Alexander Roller; Gerald Giester; Annette Rompel; Nuno Maulide
Journal:  Chemistry       Date:  2018-10-01       Impact factor: 5.236
  4 in total

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