Construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines |
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| Authors: | Chihiro Homma Aika Takeshima Taichi Kano Keiji Maruoka |
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| Institution: | Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 Japan.; Graduate School of Science, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8502 Japan.; School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006 China |
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| Abstract: | Stereoselective Mannich reactions of aldehydes with ketimines provide chiral β-amino aldehydes that bear an α-tert-amine moiety. However, the structural variation of the ketimines is limited due to the formation of inseparable E/Z isomers, low reactivity, and other synthetic difficulties. In this study, a highly diastereodivergent synthesis of hitherto difficult-to-access β-amino aldehydes that bear a chiral α-tert-amine moiety was achieved using the amine-catalyzed Mannich reactions of aldehydes with less-activated Z-ketimines that bear both alkyl and alkynyl groups.Stereoselective Mannich reactions of aldehydes with ketimines provide chiral β-amino aldehydes that bear an α-tert-amine moiety. |
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