Asymmetric Disulfonimide‐Catalyzed Synthesis of δ‐Amino‐β‐Ketoester Derivatives by Vinylogous Mukaiyama–Mannich Reactions |
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| Authors: | Dr Qinggang Wang Manuel van?Gemmeren Prof?Dr Benjamin List |
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| Affiliation: | Max‐Planck‐Institut für Kohlenforschung, Kaiser‐Wilhelm‐Platz 1, 45470, Mülheim an der Ruhr (Germany) |
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| Abstract: | An organocatalytic asymmetric synthesis of δ‐amino‐β‐ketoester derivatives has been developed. A chiral disulfonimide (DSI) serves as a highly efficient precatalyst for a vinylogous Mukaiyama–Mannich reaction of readily available dioxinone‐derived silyloxydienes with N‐Boc‐protected imines, delivering products in excellent yields and enantioselectivities. The synthetic utility of this reaction is illustrated in various transformations, including a new C? C bond‐forming reaction, which provide useful enantioenriched building blocks. The methodology is applied in a formal synthesis of (?)‐lasubin. |
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| Keywords: | δ ‐amino‐β ‐ketoesters disulfonimides organocatalysis vinylogous Mukaiyama– Mannich reaction |
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