Rhodium-Catalyzed Enantioselective Addition of Organoaluminum Reagents to N-Tosyl Ketimines

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• 作者：Sebastian Hirner ; Andreas Kolb ; Johannes Westmeier ; Sandra Gebhardt ; Stephen Middel ; Klaus Harms ; Paultheo von Zezschwitz
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：June 6, 2014
• 年：2014
• 卷：16
• 期：11
• 页码：3162-3165
• 全文大小：306K
• 年卷期：v.16,no.11(June 6, 2014)
• ISSN：1523-7052

文摘

Rhodium(I)/Binap complexes catalyze highly enantioselective additions of methyl- and arylaluminum reagents to cyclic 伪,尾-unsaturated N-tosyl ketimines. Depending on the solvent and substituents at the ring, the reaction occurs either in a 1,2-manner to deliver 伪-tertiary allylic amines or in a 1,4-manner to yield, after subsequent reduction, 3-substituted cycloalkyl amines. Well known in the case of the respective cycloalkenones, these first transformations of the aza-analogues enable the synthesis of amine structures of pharmaceutical and biochemical interest.