4.8 Article

Enantioselective Cyclization of 4-Alkenoic Acids via an Oxidative Allylic C-H Esterification

Journal

ORGANIC LETTERS
Volume 13, Issue 13, Pages 3506-3509

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol201314m

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Funding

  1. JSPS [22350041]
  2. Grants-in-Aid for Scientific Research [22350041] Funding Source: KAKEN

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An enantioselective intramolecular oxidative cyclization of 4-alkenoic acids was developed. The reaction proceeded via a pi-allyl Pd intermediate generated by an allylic C-H activation to give gamma-lactone derivatives with moderate to good enantioselectivity. Spiro bis(isoxazoline) ligand, SPRIX, was indispensable for this asymmetric transformation.

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