Enantioselective Allylation of Ketones Catalyzed by N,N'-Dioxide and Indium(III) Complex

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• 作者：Xin Zhang ; Donghui Chen ; Xiaohua Liu ; Xiaoming Feng
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：July 6, 2007
• 年：2007
• 卷：72
• 期：14
• 页码：5227 - 5233
• 全文大小：239K
• 年卷期：v.72,no.14(July 6, 2007)
• ISSN：1520-6904

文摘

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Complexes of (S)-pipecolic acid-, L-proline-, and other amino acid-derived N,N'-dioxides coordinatedwith different metal ions have been investigated in the enantioselective allylation of ketones. A varietyof aromatic ketones were found to be suitable substrates in the presence of the L1-In(III) complex, andafforded the corresponding homoallylic alcohols with good enantioselectivites (up to 83% ee) and moderateto high yields (up to 94%). On the basis of the experimental results, a possible catalytic cycle includinga transition state has been proposed to explain the origin of the reactivity and asymmetric inductivity,and a bifunctional catalyst was described with Lewis base N-oxide activating tetraallyltin and Lewis acidindium activating ketone.