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Pd-Catalyzed Acyl C–O Bond Activation for Selective Ring-Opening of α-Methylene-β-lactones with Amines

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Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States
Cite this: Org. Lett. 2017, 19, 8, 1966–1969
Publication Date (Web):April 4, 2017
https://doi.org/10.1021/acs.orglett.7b00494
Copyright © 2017 American Chemical Society

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    Abstract

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    A Pd-catalyzed ring-opening of β-lactones with various types of amines (primary, secondary, and aryl) to provide β-hydroxy amides with excellent selectivity toward acyl C–O bond cleavage is reported. The utility of this protocol is demonstrated in an asymmetric kinetic resolution providing enantioenriched α-methylene-β-lactones.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.7b00494.

    • Detailed experimental procedures, analytical and spectral data for all new compounds, and HPLC traces for kinetic resolution experiments (PDF)

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