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δ-amino-β-ketoesters; disulfonimides; organocatalysis; vinylogous Mukaiyama–Mannich reaction
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.
