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  • Title: Enantioselective cyanation/Brook rearrangement/C-acylation reactions of acylsilanes catalyzed by chiral metal alkoxides.
    Author: Nicewicz DA, Yates CM, Johnson JS.
    Journal: J Org Chem; 2004 Oct 01; 69(20):6548-55. PubMed ID: 15387576.
    Abstract:
    New catalytic enantioselective cyanation/1,2-Brook rearrangement/C-acylation reactions of acylsilanes (4) with cyanoformate esters (7) are described. The products of the reaction are fully substituted malonic acid derivatives (8). Catalysts for this transformation were discovered via a directed candidate screen of 96 metal-ligand complexes. Optimization of a (salen)aluminum complex revealed significant remote electronic effects and concentration effects. The scope of the reaction was investigated by using a number of aryl acylsilanes and cyanoformate esters. Chemoselective reduction of the reaction products (8) afforded new enantioenriched alpha-hydroxy-alpha-aryl-beta-amino acid derivatives (32-34) and beta-lactams (35 and 36). This reaction provides a simple method for the construction of new nitrogen-containing enantioenriched chiral building blocks.
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