4.8 Article

Copper(I)-Catalyzed Enantioselective 1,6-Borylation of α,β,γ,δ-Unsaturated Phosphonates

Journal

ORGANIC LETTERS
Volume 20, Issue 24, Pages 7961-7964

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03532

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Funding

  1. National Research Foundation of Korea (NRF) [2016R1A2B4011719, 2016R1A4A1011451]
  2. Korea government (MEST)
  3. National Research Foundation of Korea [2016R1A2B4011719] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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Copper(I)-catalyzed asymmetric 1,6-borylation of 1,3-dienylphosphonates was achieved using (S,S)-Ph-BPE as a chiral ligand. Regio-, stereo-, and enantioselective borylation successfully proceeded to afford phosphonate-containing allylboronates, with high enantioselectivity up to 97% ee. Further applications of the resulting products generated a valuable phosphonate analogue of gamma-butyrolactone.

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