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Phase-Transfer Catalysis via a Proton Sponge: A Bifunctional Role for Biscyclopropenimine

Lee Belding, Peter Stoyanov and Travis Dudding*

*Brock University, 500 Glenridge Avenue, St. Catharines, ON L2S 3A1 Canada, Email:

L. Belding, P. Stoyanov, T. Dudding, J. Org. Chem., 2016, 81, 553-558.

DOI: 10.1021/acs.joc.5b02395


A bis(diisopropylamino)cyclopropenimine-substituted bis-protonated proton sponge can be used as a bifunctional phase-transfer catalyst. The catalyst operates simultaneously as a hydrogen bond donor and a phase-transfer catalyst, facilitating the movement of charged intermediates from the interface to the organic phase.

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Key Words

O'Donnell Amino Acid Synthesis, benzylation, allylation

ID: J42-Y2016