ORGN 292 |
Thiazolium-catalyzed reactions of acylsilanes: New strategies for acyl anion addition reactions
| Anita E. Mattson and Karl A Scheidt. Department of Chemistry, Northwestern University, 2145 Sheridan Rd, Evanston, IL 60208 |
| A new strategy for catalytic acyl anion additions using organic catalysts has been developed. Neutral carbenes (or zwitterions) generated in situ from available thiazolium salts are effective catalysts for the reactions of acylsilanes and various electrophiles. The use of heterocyclic carbenes is in contrast to established anionic catalysts typically employed to promote the required Brook rearrangement (1,2-silyl shift from carbon to oxygen). The acyl anions generated by this method are not reactive with the acyl anion precursor and can be added to unsaturated conjugate acceptors to generate highly useful 1,4-dicarbonyl compounds as well as added to protected imines to afford alpha-amino ketones. The development of this methodology, studies of substrate scope and potential mechanisms will be discussed. 
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