Literature DB >> 12105887

Face-selective addition to a cation-pi complex of a pyridinium salt: synthesis of chiral 1,4-dihydropyridines.

Shinji Yamada1, Chisako Morita.   

Abstract

Selective shielding of one side of the pyridinium face by way of intramolecular cation-pi complex formation enabled nucleophiles to attack only from the non-shielded side, and consequently, chiral 1,4-dihydropyridines were produced stereoselectively with up to 99% de. The structure of the cation-pi complex was elucidated by 1H NMR studies and X-ray analysis.

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Year:  2002        PMID： 12105887     DOI： 10.1021/ja0203317

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


  8 in total

1.  Cation-pi control of regiochemistry of intramolecular schmidt reactions en route to bridged bicyclic lactams.

Authors:  Lei Yao; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2007-02-16       Impact factor: 15.419

2.  Highly stereoselective ring expansion reactions mediated by attractive cation-n interactions.

Authors:  Timothy Ribelin; Christopher E Katz; Donna G English; Sherriel Smith; Anna K Manukyan; Victor W Day; Benjamin Neuenswander; Jennifer L Poutsma; Jeffrey Aubé
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Ammonium catalyzed cyclitive additions: evidence for a cation-π interaction with alkynes.

Authors:  Edith Nagy; Elijah St Germain; Patrick Cosme; Pradip Maity; Andrew C Terentis; Salvatore D Lepore
Journal:  Chem Commun (Camb)       Date:  2016-02-07       Impact factor: 6.222

4.  Mild and selective hydrozirconation of amides to aldehydes using Cp2Zr(H)Cl: scope and mechanistic insight.

Authors:  Jared T Spletstoser; Jonathan M White; Ashok Rao Tunoori; Gunda I Georg
Journal:  J Am Chem Soc       Date:  2007-02-22       Impact factor: 15.419

5.  Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones.

Authors:  Heloise Brice; Jonathan Clayden; Stuart D Hamilton
Journal:  Beilstein J Org Chem       Date:  2010-03-02       Impact factor: 2.883

6.  Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

7.  Asymmetric Cu-Catalyzed 1,4-Dearomatization of Pyridines and Pyridazines without Preactivation of the Heterocycle or Nucleophile.

Authors:  Michael W Gribble; Sheng Guo; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-04-06       Impact factor: 15.419

8.  Dearomative Synthetic Entry into the Altemicidin Alkaloids.

Authors:  Claire S Harmange Magnani; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2021-05-21       Impact factor: 16.383
  8 in total

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