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

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 in...

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Bibliographic Details
Published in:Organic letters 2011-07, Vol.13 (13), p.3506-3509
Main Authors: Takenaka, Kazuhiro, Akita, Mitsutoshi, Tanigaki, Yugo, Takizawa, Shinobu, Sasai, Hiroaki
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201314m