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Morita-Baylis-Hillman Reaction of α,β-Unsaturated Ketones with Allylic Acetates by the Combination of Transition-Metal Catalysis and Organomediation

Ya-Qiong Li, Hai-Jun Wang and Zhi-Zhen Huang*

*Department of Chemistry, Zhejiang University, Hangzhou 310028, China, Email: huangzhizhenzju.edu.cn

Y.-Q. Li, H.-J. Wang, Z.-Z. Huang, J. Org. Chem., 2016, 81, 4429-4433.

DOI: 10.1021/acs.joc.6b00684 (free Supporting Information)


Abstract

An intermolecular Morita-Baylis-Hillman (MBH) reaction of α,β-unsaturated ketones with allylic acetates in the presence of tributylphosphine, acetic acid, and catalytic amounts of tetrakis(triphenylphosphine)palladium(0) affords α-coupling products in good yields. The reaction offers good functional group tolerance, excellent regioselectivity and E-stereoselectivity.

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Key Words

Baylis-Hillman Reaction, Allylation, Baylis-Hillman Adducts


ID: J42-Y2016