Highly diastereoselective Morita-Baylis-Hillman chemistry: a remote activation effect in the diastereoface selective synthesis of densely functionalized branched cyclic enones from d-glucose

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• 作者：Vikas Kumar ; Partha Ghosal ; Pintu Das ; Arun K. Shaw ; ^{akshaw55@yahoo.com}
• 刊名：Tetrahedron ; Asymmetry
• 出版年：2012
• 期刊代码：108_09574166
• 类别：ch
• 出版时间：15 April, 2012
• 卷：23
• 期：6-7
• 页码：449-456
• 文件大小：1535 K

摘要

A highly diastereoselective C-2 alkylation of sugar derived cyclic enone 1 in the presence of diethylaluminium iodide by utilizing Morita-Baylis-Hillman chemistry is reported. While diethylaluminium iodide was found to be a suitable Lewis acid for this transformation, the widely employed TiCl₄ was ineffective. A plausible mechanism, which considered the involvement of a Zimmerman-Traxler type of closed transition state and an orthoester intermediate, has been discussed.