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Xian-Shuang Tu1, Ning-Ning Zeng1, Ru-Ye Li1

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Angewandte Chemie (International Ed. in English)
|September 14, 2018
PubMed
Summary
This summary is machine-generated.

New chiral bicyclic bisborane catalysts were synthesized for imine hydrogenation. These catalysts show high activity and enantioselectivity, enabling efficient asymmetric synthesis.

Keywords:
asymmetric catalysisboronfrustrated Lewis pairshomogeneous catalysishydrogenation

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Asymmetric Synthesis

Background:

  • Chiral catalysts are crucial for enantioselective synthesis.
  • Borane chemistry offers unique catalytic possibilities.
  • Developing novel catalysts with improved efficiency and selectivity is ongoing.

Purpose of the Study:

  • To synthesize a new class of chiral C2-symmetric bicyclic bisborane catalysts.
  • To investigate the influence of reaction temperature on catalyst diastereoselectivity.
  • To evaluate the catalytic performance of the synthesized bisboranes in imine hydrogenation.

Main Methods:

  • Addition reactions of internal dienes with Piers borane (HB(C6F5)2) and its analogue (HB(p-C6F4H)2).
  • Control of reaction temperature to achieve selective diastereomer formation.
  • In situ preparation and application of bisborane catalysts in imine hydrogenation.

Main Results:

  • Successful preparation of chiral C2-symmetric bicyclic bisborane catalysts.
  • Selective synthesis of two diastereomeric catalysts from a single diene precursor by temperature control.
  • High catalytic activity (turnover numbers up to 200 at -40°C) and enantioselectivity (up to 95% ee) in imine hydrogenation.

Conclusions:

  • The new bisborane catalysts are effective for asymmetric imine hydrogenation.
  • Diastereoselective synthesis is achievable through temperature-dependent addition reactions.
  • These catalysts represent a promising advancement in chiral catalysis for organic synthesis.