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Catalytic Additions of Acylsilanes to Imines:  An Acyl Anion Strategy for the Direct Synthesis of α-Amino Ketones

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journal contribution
posted on 11.11.2004, 00:00 by Anita E. Mattson, Karl A. Scheidt
The addition of acylsilanes to imines catalyzed by neutral carbenes (or zwitterions) generated in situ from readily available thiazolium salts is described. The general reaction successfully utilizes acylsilanes as carbonyl anion precursors and is tolerant of a range of structural diversity on the acylsilane or imine electrophile. The overall reaction utilizes easily available precursors and directly accesses protected α-amino ketones in the correct oxidation state.