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

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journal contribution
posted on 01.07.2011, 00:00 authored by Kazuhiro Takenaka, Mitsutoshi Akita, Yugo Tanigaki, Shinobu Takizawa, Hiroaki Sasai
An enantioselective intramolecular oxidative cyclization of 4-alkenoic acids was developed. The reaction proceeded via a π-allyl Pd intermediate generated by an allylic C–H activation to give γ-lactone derivatives with moderate to good enantioselectivity. Spiro bis(isoxazoline) ligand, SPRIX, was indispensable for this asymmetric transformation.