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Functionalized Chiral Ionic Liquid Catalyzed Asymmetric S(N)1 alpha-Alkylation of Ketones and Aldehydes

  作者 ZHANG LONG; CUI LINGYUN; LI XIN; LI JIUYUAN; LUO SANZHONG; CHENG JINPEI  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2010年-25;  页码  4876-4885  
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[摘要]Pyrrolidine-derived functionalized chiral ionic liquids (FCILs) have been found to catalyze asymmetric S(N)1 alpha-alkylations of ketones and aldehydes with up to 99% yield, >99:1 dr and 87% ee. The FCIL catalysts enable S(N)1 alpha-alkylations of cyclic ketones, particularly of 3- and 4-substituted cyclohexanones with excellent diastereoselectivity and good enantioselectivity, featuring unprecedented desymmetrization and kinetic resolution processes for these types of asymmetric reaction. Full details of this study as well as the proposed enamine transition-state are presented.

 
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