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DABO Boronate Promoted Conjugate Allylation of α,β-Unsaturated Aldehydes Using Copper(II) Catalysis

Pjotr C. Roest, Nicholas W. M. Michel and Robert A. Batey*

*Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, Canada M5S 3H6, Email: rbateychem.utoronto.ca

P. C. Roest, N. W. M. Michel, R. A. Batey, J. Org. Chem., 2016, 81, 6774-6778.

DOI: 10.1021/acs.joc.6b00782 (free Supporting Information)


Abstract

In a catalytic method for the regioselective allylation of α,β-unsaturated aldehydes, the use of an air-stable diethanolamine-complexed boronic acid (DABO boronate) as the allyl transfer reagent promotes conjugate addition over 1,2-addition. Various aryl- and alkyl-substituted enals provide δ,ε-unsaturated aldehyde products in good yields under mild conditions.

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Key Words

allylation, carbonyl compounds


ID: J42-Y2016