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Asymmetric Disulfonimide-Catalyzed Synthesis of δ-Amino-β-Ketoester Derivatives by Vinylogous Mukaiyama–Mannich Reactions

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Wang,  Qinggang
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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van Gemmeren,  Manuel
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Wang, Q., van Gemmeren, M., & List, B. (2014). Asymmetric Disulfonimide-Catalyzed Synthesis of δ-Amino-β-Ketoester Derivatives by Vinylogous Mukaiyama–Mannich Reactions. Angewandte Chemie International Edition, 53(49), 13592-13595. doi:10.1002/anie.201407532.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-76B2-4
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.