4.7 Article

Iron-catalysed enantioselective carbometalation of azabicycloalkenes

期刊

CHEMICAL COMMUNICATIONS
卷 57, 期 57, 页码 6975-6978

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc02387j

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资金

  1. JSPS through the `Funding Program for Next Generation World-Leading Researchers (NEXT Program)' [CREST 1102545]
  2. ALCA from the Japan Science and Technology Agency (JST)
  3. JSPS Core-to-Core Program' Elements Function for Transformative Catalysis and Materials'
  4. JSPS KAKENHI [20H02740]
  5. JSPS
  6. MEXT project 'Integrated Research Consortium on Chemical Sciences'
  7. SERB, DST, Govt. of India [SRG/2020/001350]
  8. WBDST-BT [1854 (Sanc.)/ST/P/ST/15G-7/2019]
  9. International Collaborative Research Program of Institute for Chemical Research, Kyoto University [2019-20, 2020-16]
  10. JURC at ICR, Kyoto University
  11. Grants-in-Aid for Scientific Research [20H02740] Funding Source: KAKEN

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The first enantioselective carbometalation reaction of azabicycloalkenes has been achieved by iron catalysis to form optically active organozinc intermediates, showing the direct coordination of the chiral phosphine ligand to the iron center during bond formation. This new class of iron-catalyzed asymmetric reaction will contribute to the synthesis and production of bioactive molecules.
The first enantioselective carbometalation reaction of azabicycloalkenes has been achieved by iron catalysis to in situ form optically active organozinc intermediates, which are amenable to further synthetic elaborations. The observed chiral induction, along with the DFT and XAS analyses, reveals the direct coordination of the chiral phosphine ligand to the iron centre during the carbon-carbon and carbon-metal bond forming step. This new class of iron-catalysed asymmetric reaction will contribute to the synthesis and production of bioactive molecules.

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