4.8 Article

Asymmetric Chlorination/Ring Expansion for the Synthesis of α-Quaternary Cycloalkanones

Journal

ORGANIC LETTERS
Volume 16, Issue 6, Pages 1810-1813

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol5005565

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Funding

  1. National Basic Research Program of China (973 Program) [2010CB833300]
  2. National Natural Science Foundation of China [21025209, 21121062, 21361140373]
  3. Chinese Academy of Sciences

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A highly enantioselective chlorination/ring expansion cascade for the construction of cycloalkanones with an all-carbon quaternary center was realized (up to 97% ee). Oxa-cyclobutanol substrates were employed for the first time in the ring expansion reactions, affording the functionalized dihydrofuranones in excellent enantioselectivity.

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