Development of Biisoquinoline-Based Chiral Diaminocarbene Ligands: Enantioselective SN2' Allylic Alkylation Catalyzed by Copper-Carbene Complexes

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• 作者：Hwimin Seo ; Dimitri Hirsch-Weil ; Khalil A. Abboud ; Sukwon Hong
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：March 7, 2008
• 年：2008
• 卷：73
• 期：5
• 页码：1983 - 1986
• 全文大小：167K
• 年卷期：v.73,no.5(March 7, 2008)
• ISSN：1520-6904

文摘

Chiral biisoquinoline-based diaminocarbene ligands (BIQ)were designed to create a chiral environment extended towardthe metal center, which was confirmed by an X-ray structure.The concise ligand synthesis is highlighted by a modifiedBischler-Napieralski cyclization of bisamides prepared fromreadily available chiral phenethylamines, and allows easyvariation of the stereodifferentiating groups. The cyclohexyl-BIQ-copper complex is an efficient catalyst for enantioselective S_N2' allylic alkylation with Grignard reagents showingS_N2' regioselectivity higher than 5:1 and enantioselectivityin the range of 68-77% ee.