4.8 Article

Catalytic, Enantioselective Synthesis of Allenyl Boronates

Journal

ACS CATALYSIS
Volume 8, Issue 4, Pages 3650-3654

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b00626

Keywords

allenes; asymmetric catalysis; enynes; homogeneous catalysis; hydroboration

Funding

  1. Nankai University College of Chemistry
  2. TSRI
  3. Pfizer, Inc.
  4. Bristol-Myers Squibb
  5. National Institutes of Health [1R35GM125052]
  6. NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R35GM125052] Funding Source: NIH RePORTER

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A method to achieve enantioselective 1,4-hydroboration of terminal and internal enynes to access allenyl boronates under CuH catalysis is described. The reaction typically proceeds in a highly stereoselective manner and tolerates an array of synthetically useful functional groups. The utility of the enantioenriched allenyl boronate products is demonstrated through several representative downstream derivatizations.

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