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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Asymmetric Henry Reaction Using Cobalt Complexes with Bisoxazoline Ligands Bearing Two Fluorous Tags.

Kazuki Ishihara1, Yamato Kato1, Narisa Takeuchi1

  • 1Faculty of Agriculture, Meijo University, 1-501, Shiogamaguchi, Tempaku-ku, Nagoya 468-8502, Japan.

Molecules (Basel, Switzerland)
|November 25, 2023
PubMed
Summary

Fluorous tags in bisoxazoline ligands reversed stereoselectivity in cobalt-catalyzed asymmetric Henry reactions. This effect, driven by the fluorous tags, was more pronounced than with alkyl chains.

Keywords:
Henry reactionabsolute configurationfluorousligandoxazoline

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Area of Science:

  • * Organic Chemistry
  • * Asymmetric Catalysis
  • * Organometallic Chemistry

Background:

  • * The Henry reaction (nitroaldol reaction) is a key carbon-carbon bond-forming reaction.
  • * Asymmetric catalysis enables the synthesis of enantiomerically enriched compounds.
  • * Bisoxazoline ligands are widely used in asymmetric catalysis.

Purpose of the Study:

  • * To investigate the impact of fluorous tags on bisoxazoline ligands.
  • * To determine the effect of these modified ligands on stereoselectivity in cobalt-catalyzed asymmetric Henry reactions.
  • * To compare the influence of fluorous tags versus alkyl chains on reaction outcomes.

Main Methods:

  • * Synthesis of bisoxazoline ligands with and without fluorous tags.
  • * Cobalt-catalyzed asymmetric Henry reaction using these ligands.
  • * Analysis of stereoselectivity using chiral chromatography or spectroscopy.

Main Results:

  • * Bisoxazoline ligands with two adjacent fluorous tags induced a reversed stereoselectivity compared to nonfluorous analogs.
  • * Replacing fluorous tags with alkyl chains of similar length also reversed stereoselectivity, but to a lesser extent.
  • * The presence of fluorous tags significantly influenced the stereochemical outcome.

Conclusions:

  • * Fluorous tags on bisoxazoline ligands can effectively control and reverse stereoselectivity in cobalt-catalyzed asymmetric Henry reactions.
  • * The unique properties of fluorous tags play a crucial role in modulating catalytic activity and selectivity.
  • * This study highlights a novel strategy for tuning asymmetric catalysis using fluorinated ligands.