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Highly Diastereoselective Preparation of Aldol Products Using New Functionalized Allylic Aluminum Reagents

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journal contribution
posted on 07.02.2014, 00:00 by Zhi-Liang Shen, Zhihua Peng, Chun-Ming Yang, Julian Helberg, Peter Mayer, Ilan Marek, Paul Knochel
Chloro-substituted triethylsilyl enol ethers derived from cyclo­hexanone and related ketones are converted with aluminum powder in the presence of indium trichloride to functionalized allylic aluminum reagents which represent a new type of synthetic equivalent of metal enolates. These allylic organometallics undergo highly diastereo­selective additions to aldehydes and methyl aryl ketones, giving aldol products with a β-quaternary center.