Catalytic Dehydrative Lactonization of Allylic Alcohols

Ji Liu, Romain J. Miotto, Julien Segard, Ashley M. Erb and Aaron Aponick*

*Florida Center for Heterocyclic Compounds and Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States, Email: aponickchem.ufl.edu

J. Liu, R. J. Miotto, H. Segard, A. M. Erb, A. Aponick, Org. Lett., 2018, 20, 3034-3038.

DOI: 10.1021/acs.orglett.8b01063

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Abstract

Mild Au(I)- and Pd(II)-catalyzed S_N2' reactions of readily prepared allylic alcohols enable a convenient strategy for the synthesis of phthalides and γ-butyrolactones. Using these catalysts, exclusive formation of the desired five-membered lactones is observed without formation of undesired seven-membered rings via competing direct lactonization pathways.

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Key Words

phthalides

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ID: J54-Y2018