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Mild and Ligand-Free Pd(II)-Catalyzed Conjugate Additions to Hindered γ-Substituted Cyclohexenones

James A. Jordan-Hore, James N. Sanderson and Ai-Lan Lee*

*School of Engineering and Physical Sciences, Heriot-Watt University, Edinburgh EH14 4AS, Scotland, United Kingdom, Email: a.leehw.ac.uk

J. A. Jordan-Hore, J. N. Sanderson, A.-L. Lee, Org. Lett., 2012, 14, 2508-2511.

DOI: 10.1021/ol300794a (free Supporting Information)


Abstract

Ligand-free cationic Pd(II) catalyst is a highly active catalytic system for conjugate additions of boroxines to sterically hindered γ-substituted cyclohexenones in the presence of NaNO3 as an additive. More challenging γγ- and βγ-substrates also react well to produce products with quaternary centers in a highly diastereoselective fashion.

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Key Words

Cyclohexanones, 1,4-addition


ID: J54-Y2012-1570